Short and Pointy
Copyright© 2019 by DarkMatter
Educating Anna
BDSM Sex Story: Educating Anna - Collection of short stories featuring extreme s&m but no plot. If blood and very hard pain are not your thing, turn around now. You have been warned. Please do not downvote the story just because it does not match your particular brand of kink. Also remember the difference between reality, fantasy-I-wish-would-become-reality, and pure fantasy.
Caution: This BDSM Sex Story contains strong sexual content, including Ma/Fa Fa/Fa Consensual Lesbian Heterosexual Sister BDSM MaleDom Rough Sadistic Spanking Torture Anal Sex Fisting Oral Sex Sex Toys Water Sports Needles
Author’s note: This chapter is very extreme. Don’t do this at home, or you’ll need a very good laywer.
Hi, it’s me again, Bella. Did you read about my sister’s ‘mistake’? Anna is such a moron sometimes. She is always getting into trouble, but this time she could have really been hurt. Do you have any idea how fast you dehydrate when you are wet and leaking all the time? So I’ll drive the message home today, I’ll give her a session that she won’t forget, and that will hopefully keep her out of mischief for a while.
I’ve already tied her to her luxury cross. The cross is standing upright, so I have easy access to her entire front. She is also gagged. I used several safety pins to close her mouth, so she is bleeding just a bit from her lips. But no matter, there will be more blood later, I’m sure. I will only torture her and give her some anal stimulation - no clit rubbing or cunt fucking or anything like that. So she either cums from that, or not at all.
First order of business: tie off her tits. Her large udders are sagging a bit, but not for long. I use a thin rope and tie them very tight. Then I use a second rope and tie them even tighter. Their base is very constricted by now, but still I remove the first rope (which is neither easy nor painless, since it’s partially below the second one). And then I use the first rope again to tie the base even more. I have to use all my strength, but it’s worth the effort. Because now, her flesh is constricted enough for what I have in mind: handcuffing her tits! Or is that titcuffing? Anyway, I put a pair of handcuffs on her mammaries. I also take off the rope, because that’s not needed any more. Her jugs are already swelling up nicely, with her blood firmly trapped behind the cuffs.
Second order of business: pump her clit. With a small suction cup and a strong hand pump, I quickly suck her little nub into the vacuum tube. But that’s not all, of course, so I keep pumping until her flesh is straining to the maximum, trying to take the place of the air that has evacuated the tube. I leave her like this for a few minutes while I get myself a drink.
When I get back, I loosely tie a thin cord around her clit on top of the vacuum cup, then I take off the cup and quickly fasten the cord tightly around her grossly swollen clit. So now her tits and her clit are bulging out of their constraints. But her tits are a lot redder than her clit, which brings us to the...
Third order of business: pepper her clit. I’m using our chili ointment, for the extra ooomph. So I put that on her clit, which is now quickly turning a deep shade of angry red.
So that’s the preparation done. Anna is quietly crying in her bonds. Serves her right, the moron!
Do you know what hurts more than having burning chili on your tender bits? Touching those bits! For some reason, the burning gets much more intense when the flesh is in contact with something. So grabbing and pinching her clit between my fingers (I’m wearing latex gloves, of course) must be intense. I’m not sure how it feels when I trap her clit between two small metal bars and screw them together, squashing Anna’s clit flat.
Now that her clit is taken care of, and certainly not the source of any pleasant sensations, I start with the actual session.
With some lube I deftly insert a medical catheter into my twin’s urethra, right up to her bladder. There is a small inflatable ball at the end that ensures that it does not slip back out. This catheter has three functions: first, it blocks anything from coming out. Second, it empties the bladder, no matter what my sister wishes. And third, you can force-feed stuff into the bladder. Which is what I do: with a large syringe, I fill her bladder with ice-water. Before that, I make sure her bladder is nice and empty by removing all her piss into a bowl. I have another large bowl of water with ice cubes prepared. From this I fill the syringe, and then I push the near-freezing water into the catheter and thus into Anna’s bladder. Then I do it again. Two more loads fill her bladder to the bursting point. And then I close the catheter, so nothing can escape.
I recently bought a new dildo. It’s not very thick, but it’s about as long as my arm, so I’ve christened it ‘Anaconda’. I think it is time that I introduced Anna to Anaconda.
As she’s tied to the cross, getting to her ass is a bit awkward, but if I don’t care much about her comfort (I don’t), then it is doable. Anaconda is slippery with lube and the tip slides in very easily. It gets a lot more tricky after that, not because it doesn’t fit, but because it keeps slipping through my fingers. Finally I get a strong grip on the end with one hand and use that to push upward, and with the other hand I sort of guide it in. This works very well, and in short order the entire snake has disappeared into my twin’s ass. Her squirming has increased, but I’m not sure if that’s because of Anaconda or because of the chili.
Now I just have to get back to her tits. They are huge and dark and spectacular. I cannot resist (and why should I?) and I take my time liking her swollen milkjugs. That’s nice. You know what’s nicer? Needles in her nips! Lots of them, and large ones, too. Not the tiny thin “I-barely-know-they’re-there” kind of needles, but the heavy gauge “I-could-use-’em-on-a-horse” kinda needles. Well, maybe not a horse, but they are pretty thick, and I know from experience that they hurt a lot going in and also coming back out. So I put about a dozend in each of her buds. I woulda have used more, but I ran out of room. But hey, look at those tiny hedgehogs on top of her tits. Neat!
But now it’s been long enough that I have to renew the chili ointment. You didn’t think that would last forever, did you? No, it only lasts for about a quarter hour, then the sting lessens a lot. And we certainly don’t want that, do we? So I unscrew the metal bars, re-apply the chili oil, and screw the bars back in place. Anna just loves this, I’m sure. Well, pretty sure, anyway.
Did I mention that I want her to suffer? Yeah, well. How do you get a painslut like her to really suffer? You up the pain, of course! Up and up and up. So the needles are nice, but they’re just the first step. Because now I’m getting rid of them all (that’s quite a mess, I can tell you, but luckily I don’t mind blood). Instead, I put a metal alligator clamp with sharp teeth and a strong spring on each nipple. These hurt a lot by themselves (as I know all too well), but on top of nipples that are already very sore? They are pure torture! Which is just what the doc ... er the sister ordered.
You know what’s even more painful than having cruel metal clamps biting into your inflamed and bleeding nipples? Having a riding crop liberally applied to those clamps, making them dance around like they are on fire! Hm, fire ... there’s an idea. Well, maybe later. For now, the crop. Oh, I’m not just hitting her nips, I’m also hitting her clit. You know, right on the metal bars, putting even more pressure on the flesh cooking in chili oil.
The riding crop is originally used for horses and other animals, which is fitting considering the animal noises Anna is making through the safety pins keeping her mouth shut. I don’t want to overdo it, which is why I only hit her for about 10 minutes or so. From the way she tries to rip the cross out of its mount you’d think I’d been at it for hours.
All right, that’s enough of that (I don’t want her to actually shake the cross loose). Now I even take off the clamps (I’m nice like that) and enjoy the new sounds she makes as the blood rushes back into the crushed flesh.
Speaking of blood: time for a new set of needles. Same size, and another dozend for each side. Anna is white as a sheet now, and I don’t think it’s from the blood loss, there just isn’t enough of that. I think she has finally realised that today any limits we used to have are out the window, through the woods, and drowned in the lake behind the woods. So I take my sweet time pushing the new needles in, looking into her eyes as much as I can and savouring the fear and suffering I see there.
And now it’s time again for a new layer of chili.
Once that’s applied, I take out the needles again. They have served their purpose: Anna’s breast peaks are on fire! But now comes the true test. I loosen her restraints and take her off the cross. She could now force and end to the session if she really wanted to. I just point her to a wooden board that’s fastened between two metal poles at about belly height.
My sister quickly looks at me, then at the board, and then she quickly moves over and squats in front of it, putting her tits on top of the wood. Yep, that’s what I thought.
Out comes a hammer and two nails, and I nail her nipples to the board. Actually I put the nails slightly behind the nipples to get more purchase and not to actually damage the bleeding nubs too much.
This puts Anna in an awkward position, as the board is too high for her to kneel and to low for her to stand. She has to kind of bend her knees and hunch over. But that’s all I do to restrain her, she is held in place by her nipples and nothing else. I briefly consider tieing her arms behind her back, but this is better. She can move everything, yet is completely immobile.
I have her lift her left foot and put several bottle caps beneath the sole (sharp side up, of course). Then I do the same with her other foot. So just standing there is quite painful now.
As much as I like my new Anaconda, it’s in the way now so I take it out. We have a large butt plug that we sometimes use. It’s very large and it always takes a lot of work to get it in. That’s what will go into Anna’s ass in stead of Anaconda. But today it won’t take long at all! But first, I have to lube it up. Guess what I use as lubricant? Well, if I’ve already got the chili out, why not use it. Right? So that’s what I smear very liberally all over the plug.
I tell my sister to seriously brace herself as I position the anal monster at her rear entrance. And then I lift a mallet, take aim, swing and force the plug in with a single hit!
I’m betting that my twin is really regretting her lack of resistance just a few minutes ago. She clearly is in agony, barely keeping herself in position so that she doesn’t rip her own nipples off. Her entire body is shaking, and she is unable to make any coherent sound through her sealed lips. But apparently she is trying, ‘cause there is a lot of blood around the safety pins that keep her mouth shut. But I don’t really want to listen to her, so I ignore that and just watch her for a while.
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