I pushed forward just the tiniest bit though from her reaction you would guess I had just shoved the whole thing in. I was not using any lube because, of course, this was meant to be a punishment and I wanted her hurting a little but I was barely a quarter in before she changed from wriggling to writhing, so much that I had to use one hand to keep her ass in place. a few seconds later I had moved to almost half an inch, her closed mouth grunts steadily raising in pitch as my dick made it further and further into her last virgin hole. it took 30 more seconds to get to a full inch, 30 seconds of steadily increasing cries and clenching, each second her writhing became stronger and stronger to where I could barely keep her in position with one hand, but I managed. at the end of the first moment, I started speaking "I am surprised how willful you are, I guess you need a bit more don't you?"
She shook her head rapidly, her eyes begging me to make it stop, she had to stop her writhing while shaking her head and I felt her shaking in my hands. Once again I almost felt sorry for her, I was sure she would come to like it eventually but for now things were going way too fast for her and it was scaring her. I felt bad, but remembered how far she had made me take it in just one day, the scene of me rubbing the skin off the tip of my dick in the bathroom at school and hiding under the dirty metal bench and I though to my self "I am not taking it any faster then her, and the pain in her ass cant be worse then the pain in my dick earlier, I need to give her some tough love and teach her what happens when she pushes people too far."
Having realized what I needed to do, I sat for a moment, just relishing the feeling of having the head of my dick inside a never before used hole, I might never get the feeling again and I wanted to enjoy it. The soft vibrations of her sobs and shaking made a great vibrating feeling as I stood, and almost got me to the point of cumming from that alone, but I held on. A moment later I knew if I stalled for much longer I would cum, so I was forced to move forward.
I thrust the rest of my dick into her ass with a single unexpected stroke, my sister's head rolled backwards and I could see her eyes roll just as far from around the side of her head, her mouth gaped open and I took my chance, shoving almost my entire cum covered hand into her mouth in a position that was no doubt uncomfortable but would keep her mouth wide enough that she could not bite down when she recovered from the pleasure.
I took a moment to think about exactly what we were doing, two kids, still in school, were committing incestuous BDSM sex, bondage, anal, and a whole slew of other things the world would consider taboo, and somehow I was loving it.
My sister woke out of her stupor a second later, none too enthused to find her mouth stretched open, she almost tried to bight down before I waved my other finger in front of her face.
"Lick" I commanded again.
She meekly nodded, no longer possessing the energy or will to resist after the last experience, and started to lazily move her tongue over my hand. "do a better job, it better come out spotless" I continued, she redoubled her efforts.
It was going to be a good week, I decided.
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