Day 31: Saturday

Today is a very special day. Oh, not because it’s Saturday, and we’ve got the whole day to play. No, not even because it’s the first day of the summer break, and we’ve got several weeks to play! No, today our mom leaves on a two-week trip, leaving me in charge and my sister completely at my mercy for two fucking weeks!!!

Of course, Anna is even more exited about it than I am. We have planned two weeks of 24/7 fun! And I’ve laid some rules that she will have to follow.

The first rule is that while we are at home, she will always be naked, and her hands will be cuffed behind her back. There is an exception to the latter part of the rule for housework, and of course during active play time I can remove the cuffs as well.

The second rule is that she is now on a diet (not that she needs it). She is allowed three meals per day, but she has to make me cum once for each one. If she can’t manage that, she’ll have to go hungry.

The third and last rule is that every session we do will start with an ass caning. The first session will start with 40 hits, then every session that number is increased by 10. 40 may not sound like much, but after two weeks it’ll be a lot more! Plus, we will do this every-single-day, so Anna will get bruises on top of bruises ... well, we’ll have to see how it goes. Actually, 40 is a compromise. Anna wanted to start at a 100, which I nixed right away. I on the other hand wanted to start at 10, but I let her talk me up to 40, which is where we will start today.

But first we have to wait for our mom to leave, which she does shortly before noon. This may sound as if we don’t like her and can’t wait to get rid of her. Nothing could be further from the truth - at least concerning the first part. We both love her very much ... but we are also impatient to get started. Also, Anna hasn’t had breakfast yet, because we can’t very well have sex while mom is at home, and Anna is only allowed food after she brings me off.

So we’re both glad when she finally says her goodbyes, admonishes me to take care of my step-sister (which I fully intend to do of course, even though keeping a straight face while assuring her of this fact is rather hard), and admonishes said step-sister to keep me out of trouble (which is deeply unfair, all things considered).

The second the door closes behind her, Anna is stripping off her clothes, and I’m fucking her right there on the floor! Maybe we both are a little too impatient ... but at least this takes the edge off for a moment, and now Anna can have breakfast (or rather an early lunch) in peace. I’m allowing her some cereal with milk, which she is slurping directly from the bowl, because - as you might remember - she has to be handcuffed all the time!

The weather is very nice, so we decide (actually, I decide, and Anna grunts her approval through a mouth full of milky cereal) to go outside. We’ll go back to ‘our’ clearing, but to save time we will take out bikes and ride most of the way. Only the last bit is too rough for the bikes, so we will have to walk that part.

To make the ride more interesting, my little sister will be filled with not one, but two dildos: one in each hole. And no, I’m not talking about her mouth. Actually, I thought about adding a third dildo for that, but it wouldn’t really be practical during the ride. Instead, I make her carry the backpack with all the toys that we are taking with us. I packed it while she was eating, so she doesn’t know what’s inside - except for the cane, because the end is sticking out. But she already knew that she would be caned.

As she shoulders the backpack (I’ve taken off her cuffs for the ride), she also notices that it is quite heavy. She throws me a questioning look, but keeps silent. Keeping silent becomes more difficult during the ride, because it’s already quite hot out, and the heavy burden makes her sweat even more. Plus the two dildos that are kept in constant motion from the pedalling create some sensations of their own. I can tell that Anna is all hot and bothered, but of course she is not allowed to cum on the way.

When the path becomes too rough and overgrown for bikes, we dismount (from the bikes, Anna is still mounting her dildos) and walk the rest of the way.

Once there, we both shed out clothes and I start us off with the pre-determined caning of the sisterly ass. I have her down on all fours, raising her backside in the air. She is not restrained in any way, but I don’t expect that to be necessary.

Turns out I’m right, of course. 40 strikes on her ass, even with the cane, is not a problem for my pain-loving step sister. She wriggles a bit, and her ass is deep red with several darker lines when we are done, but she didn’t even make a sound. Well, not during the caning. She is making some now, in the form of “I told you 40 were not enough!”

Of course I know that 40 are not enough, not on the first day anyway. I’m also not worried about the second day, or the third. But I’m worried about the second week, when the accumulated damage is met with an accumulated number of much more than 40 strikes. I keep that to myself, however. You know what they say: he who laughs last ... didn’t get the joke? No, that’s not quite right. But something like that.

No matter. I don’t answer her directly, but I do make her shut up - by taking the dildos out of her nether holes and using one of them (the one from her ass, to be precise) as a gag. She has to swallow it to the base, so that only the fake balls remain outside of her mouth and throat.