Day 22: Wednesday

Wednesday is a good day for tit-torture, don’t you agree? Of course, that’s true for any day, but it’s also true for Wednesdays. So, tit-torture is on the menu today!

Usually, when we play, we to it naked. So when I ask Anna if she has any bras that she wants to throw out, she is a bit surprised. But then she manages to come up with two older bras that we can use.

So, I take about 50 thumb tacks and stick them into the first bra, from the outside in. Then, I use glue to make them stick, and finally I glue the other bra on top of the first one for better stability. And now it’s time for my sister to put it on.

She does so gingerly, but all in all it does not appear to be too bad. The tacks poke into her skin, but they don’t pierce it, and since they are not very long the pressure is not that great.

Until I take out a belt and fasten it tightly around her chest, that is. Now the pressure is suddenly a lot worse, and Anna is clearly in pain. To give her something else to think about, I quickly put a medium-sized dildo up her ass. I put it in all the way, so that nothing sticks out - and hopefully, nothing will fall out, either. With her nicely filled, I tighten the belt another notch, much to Anna’s dismay. She has some trouble breathing now, with her chest as strictly compressed as it is, but she can manage.

Thus attired, I tell her to get dressed. While she complies, I do the same. And off we go for a nice walk!

It’s a nice day, and we have a nice walk, but my sister is not really able to enjoy it. She is in a lot of pain from the thumb tacks, made worse by every movement. She can only take shallow breaths, which leaves her winded after only a few minutes of walking. And apparently her ass is cramping around the dildo, unsuccessfully trying to excep the intruder. But other than that, it’s a really nice walk.

After about half an hour we are back home, back in her room, and back to being undressed. Except for Anna’s new bra, of course.

Since she’s naked, it is easy to see that her clit is still swollen from yesterday’s ministrations. Or maybe she simply is aroused. Or both - in any case, as it is so prominent, it is easy to tie it off with a bit of twine. This causes it to swell even more. I said that today is about tit-torture, and we’ll get back to that in a minute, but first I have to torture Anna’s clit some more. I do that by polishing the engorged nub with an electric toothbrush. Based on my sister’s thrashing about, this must feel rather intense.

So I keep at it for a while.

But at some point we really need to get back to her tits. So I have her get down on all fours, but in reverse, with her belly up. It’s not an easy position, standing an hands an feet while looking upwards. And it gets even harder when I start whipping her tits with a single tail!

Of course, the double-bra softens the blows a bit, so I have to hit her extra hard. I’m not sure what this does to the thumb tacks that by now must be embedded in her flesh, but if the sounds that she makes are any indication it must be quite painful.

When I’m confident that all tacks are embedded as deeply as they can go, I abandon the whip and move over to her face. Which I then proceed to fuck as hard as I can, until I cum down Anna’s throat.

Oh, and I’m using the toothbrush on her clit again, so she cums too.