I yawned and sat up slowly. As soon as I saw the clothes I was wearing, I recalled why I had set my alarm. I grew instantly hard beneath the tight pink panties as I thought of Kate. I had to get ready - In ten minutes I knew I had to be in there and prepared for her.
I walked to the bathroom and gave my face a quick wash. I then brushed my teeth, and still having a few minutes to spare I decided to shave 'down there'. I had heard that girls liked it better shaved and I intended to make this perfect - both for myself and Kate.
Grabbing my mother's razor and shaving cream, I quickly pulled down the skirt and panties and sprayed the cool cream accross my balls and around my cock. There was very little hair to begin with down there and the shave was almost unnecessary, but I did it anyway. I then wiped away the remaining cream with a wet towel, dried myself off, ran my hands over the smoothe skin and pulled the panties and skirt back up. I was ready.
I walked out of the bathroom, over to my sister's room. I hesitated for a moment, then knocked on her door.
My sister's room? I had only imagined Kate and myself lying in bed alone, locked in a passionate embrace. I had imagined my lips touching hers, my cock embedded in her warm pussy. It had only just dawned on me that my sister would be in there with her and with this realization my entire fantasy died. Surely Kate didn't plan on making love to me with my sister sitting there watching us! It had to simply be some sort of plan to humiliate and make fun of me, laugh at me in my little sister's clothing.
I turned an began to walk back to my room, dismayed.
I heard the door creak open and Kate's soft voice, "Where ya goin' cutie?". She spoke fondly and softly, not at all the mockery I had expected.
I turned to face her, reconsidering my options - perhaps she was serious about it. As soon as I saw her, I gaped in awe. She had almost no clothing on! Other than a skimpy red bra and a matching pair of panties, Kate was entirely naked. Her body was beautiful, with full rounded breasts, well curved hips and lightly tanned skin. At her crotch I see a moist patch on the panties and as I looked back to her breasts I noted that her nipples could be seen through the bra, poking out noticably - She was obviously as aroused as I was.
Without saying another word, Kate turned and walked back into my sister's room, her plump little ass swaying forth tantilizingly. I followed her in, my eyes glued to her rear the whole way. I felt my cock twitching under the panties, still straining against the fabric needing release. I smiled, knowing my craving would soon be satisfied.
As I looked up, I noticed Sarah for the first time, sitting on the edge of her bed. Like Kate, she was clad only in a bra and panties. Hers were white and looked to be made of silk - a material which couldn't have suited her better. Above the panties she had on a strap-on. This surprised me, and my mind reeled - was Sarah a lesbian? She was blushing as I stared at it. It was about seven inches long - well over the length of my little undeveopped cock. It was made of some sort of smoothe rubber, and my sister's hand worked slowly up and down the shaft, spreading lube over it.
My eyes were fixed on Sarah with interest, but snapped quickly back to Kate as I felt her hand rubbing up against the crotch of my panties again. She led me over to the bed, had me lie down, then started to grind her hand against my little cock through the panties. I quickly grew hard beneath them, squirming in a slight discomfort as the tight fabric had it's usual effect of holding my cock in, preventing me from getting a proper erection.
I could feel Sarah's eyes on me, and heard her giggling softly as she watched. I was breathing a bit harder than usual, thrusting back eagerly against Kate's hand as it teased my cock. I shut my eyes, concentrating on the wonderful feeling. Kate's hand slowly rode up beneath my skirt to the top of the panties then slipped underneath. Her soft fingers gently squeezed in around my cock and started to stroke up and down the length of my shaft. My breathing continued to hasten as I thrusted up into her hand.
I felt Kate's other hand pushing beneath me as she masturbated me, pulling down the backside of the panties exposing my little plump butt. A single finger slowly traced down between my cheeks, rubbing against my rear entrance. I found this rather stimulating and my thrusting hastened even more into her hand, my body on the verge of orgasm.
As quickly as her hand had arrived upon my cock, it departed, letting the tight panties pull back down over my cock, encasing it back in it's prison. Kate momentarily removed her other hand as well, lightly licking her finger. I was left as I was, my eyes still shut, my hips gyrating against the open air as if I was still thrusting into her hand.
Her hand returned, rubbing against my little puckered rear entrance a few times more, then applying a gentle pressure until the now moistened finger began to push into me. While the finger was not unpleasant, it was strange. I enjoyed it, yet my erection started to subside slightly. I blushed as I thought about what Kate was doing to me with her finger, yet I did not resist. I wanted it. It felt good.
Kate grinned mischeviously up at me as the finger probed into my rear deeper. The finger swirled around in slow circles within me, stretching out my little hole a bit, while pleasuring me internally. Every so often I would feel her finger brush past a very sensitive spot (Which I later learned was called the prostate) which would cause me to shudder involuntarily, nearly triggering my orgasm each time. The finger continued to slowly rotate around my interior for a few minutes, driving me mad with lust. Eventually it's rhythm changed and it began to move in and out. As she fingered my ass, I panted with each thrust her finger made into me, so near to an orgasm, constantly almost being driven over the edge.
A second finger forced it's way in. It was a bit painful, but not too bad, and the two continued their assault. I opened my eyes, looking at Kate pleadingly. I needed to orgasm. She seemed to understand the look in my eyes, and her fingers both brushed against my prostate, then curled in, pressing against it hard. She began to massage it lightly in circles, her eyes locked on mine, watching.
I squirmed and bucked, my cock no longer even hard, but the pleasure overwhelming. I breathed in hard, a soft moan escaping my lips as my cock pulsed in the panties, leaking a few drops of cum. My entire body seemed to shudder helplessly as waves of pleasure overtook me, my hole contracting around the invasive fingers, only adding to my pleasure.
As I came down from the orgasm, the fingers continued to move slowly in and out of my rear, fingering my hole causing the entrance to stretch slightly. The feeling was pleasant and I spread my legs slightly, welcoming them to venture in deeper. I was motionless other than my fast but rhythmic breathing, still panting softly from the pleasure that Kate had given me.
Kate's fingers slowly withdrew from my hole, leaving me feeling empty but satisfied. She smiled, rubbing my limp cock through the panties. "Did my little girl like that?" she cooed, grinning at me. "Does she like having her little pussy fingered?".
I blushed. What she said was embarassing to me to say the least. At the same time however, I enjoyed what she had done and wanted to let her know. I gave a slight nod, my face flushing pink with embarassment.
"Good girl." she cooed again. Her hands slid slowly up my sides to my armpits, and she pulled me up, then hugged me tightly against her body. My face pressed in against her bra-covered breasts and I felt my erection quickly returning.
Kate stepped to the side, half-carrying me, although I'm sure I could have moved on my own. I felt another pair of hands take hold of my hips and looking back over my shoulder, I found my older sister Sarah pulling my body down to sit in her lap. Seeing no harm in sitting there, I let myself be pulled down. I had long since forgotten about the strap-on and I jolted as the smoothe lubed tip suddenly pressed up against my hole. Assisted by Kate, Sarah continued to lower my body down. The head of the strap-on was large and I whimpered softly as it forced it's way in.
It was painful, and my whimpering grew louder as it stretched out my hole. A few tears rolled from my eyes down my cheeks as I looked for help from Kate, hoping she would not let Sarah do this to me. Her eyes showed only lust and her mouth a slight grin as she kissed me and continued to push my body down onto the big rubber cock.
I tried to stand up, but Sarah's hands on my hips and Kate's on my shoulders kept me moving slowly downwards, encasing the strap-on in my rear.
In all honesty, after the initial penetration, the feeling was not at all bad. It was much like having Kate's gentle fingers in me only much larger, causing a bit more stretching at my hole. However, given the circumstance, I was panicked. I squirmed as Sarah slowly pulled me down on her cock, wanting nothing more to stand up and run away.
At last the arduous penetration came to a halt. I felt my legs against those of my sister. I felt the massive rubber cock embedded fully in my rear. Sarah's hands reached around me in a gentle embrace, making me lean back against her. I still continued to squirm slightly, much Sarah's delight, who was giggling at my obvious discomfort.
Kate seemed a bit more sympathetic, kneeling in front of Sarah. She kissed me on the lips, her fingers running down my neck, beneath the shirt to one of my nipples and giving it a light squeeze. She smiled. "Matt. Be a good little girl and sit still for us, okay?"
"For me?" She said, clasping my hand in hers and looking up into my eyes.
The pleading look on Kate's face at that moment was all I needed for persuasion. She really wanted me to behave, I knew. I really wanted her to be mine. I would have obeyed anything.
I nodded, trying to get over the discomfort, letting myself relax in my sister's lap, leaning back against her with a sigh. Sarah, sensing that I was a bit more at ease, took hold of my hips once more. She slowly began to rock her own hips, thrusting the strap-on deep into my rear. I panted softly, staring at Kate still, who smiled back as she watched.
"Good girl." Kate cooed again, softly patting me atop the head.
With each thrust, my sister pushed the strap-on deeper into my rear. After getting over the initial shock of having it used on me, the strap-on was becoming very pleasant, it's sides constantly giving a soothing, pleasureable massage to the inside of my rear. Sarah would also give occasional slaps to my butt cheeks, causing me to make sudden startled movements, while both girls giggled at me.
As Sarah filled my butt with the lovely strap-on, Kate pulled down the frontside of my panties. While normally I would have been rock-hard from the very thought of this, the penetration of my rear as well as my recent orgasm, made that impossible. Kate was instead presented - much to my dismay - with my little limp cock. She didn't seem to mind at all, as she grasped it in her hand, and slowly began to jerk me off.
The double stimulation was intense. The strap-on sped up quickly under the command of my sister and Kate was just as eager with stroking my cock. My breathing grew steadily faster and louder, interrupted by intermittant moans as the strap-on made an extra-deep thrust, or aimed just right so that it would brush against my prostate.
As I neared my orgasm, my cock began to pulsate in Kate's hand. She made a gesture to my sister, who immediately stopped thrusting. Kate's hand also stopped, leaving me a few seconds short. I wiggled my butt, trying to bounce it upon the strap-on, but Sarah held me down, not letting me finish it.
I heard Sarah say from behind me softly, "Aww, does my little girl need to cum?".
I nodded, blushing again as I continued to squirm, managing to get the strap-on pushed up against my prostate, but not really able to derive much pleasure from it without being able to make it move in and out.
Kate smiled, "Do you need to cum sweetie?" she repeated, using the same light teasing voice that my sister had used.
I blushed and nodded.
"Aww, isn't she adorable." My sister said again, watching me squirm.
Both girls grinned. "Matt, " Kate started, "tell us what you want sweetie."
"I want to cum." I groaned out, blushing red. What were they, stupid? Of course I wanted to cum!
"Oh, that's nice." Said my sister dully.
I sat, squirming, unsure of what they wanted to hear. Both girls were giggling at me in my helpless state, only adding to my embarassment, Sarah giving an occasional thrust into my ass just to keep me well-stimulated and near the orgasm.
"I need to cum!" I whimpered, trying hard to move up and down on the cock, although Sarah's hands still prohibited my movement.
"Aww. Our little girl needs to cum." Said Sarah, again in that teasing voice that was driving me mad. "But what does our little girl want?"
"I want to cum!" I repeated, feeling as if I was going to die either from embarassment or from being kept on the edge of my orgasm so long.
"Matt, " Said Kate, in a sightly less mocking voice, "What do you want Sarah to do?"
It dawned on me. Why they wanted me to say it, I don't know. Perhaps just to embarass me more. It made no difference. I wanted to cum, and I would. "I want Sarah to fuck my ass." I said, my face flushing pink.
Kate nodded, she took hold of my cock in one hand, cupping the other hand just below it's tip. I felt the strap-on quickly begin to move beneath me. Sarah worked quickly now, thrusting almost half of the length of the strap-on in and out of me each time. It took only moments for me to shudder, collapsing limply back against my sister's chest as another orgasm washed over me. My cock spurted a tiny bit of cum again, which landed in Kate's hand. The thrusting stopped quickly soon thereafter, leaving me panting breathlessly with my eyes still shut, resting my head against my sister's breasts.
Kate smiled, she lifted her cum-covered fingers to my mouth. "Open up sweetie." she cooed.
I did as she asked. Her fingers quickly found their way into my mouth. "Good girl. Now suck and swallow it all up."
Once again I obliged, tasting a salty liquid, not caring too much about what it was. Kate removed her fingers from my mouth, and I opened my eyes. "Good girl." she said again. She kissed me softly on the lips, then assisted my sister in lifting me slowly from her lap, the strap-on pulling out of me with a soft 'pop'.
The two girls left the room, giggling, leaving me on my sister's bed, still panting softly from my orgasm. I shut my eyes, and within a few minutes, sleep overtook me.
Being a girl certainly was exhausting.