Despite taking a rest from writing, I most certainly have not taken a rest from thrashing Robert’s bare bottom, as the colourful stripes he is currently sporting will testify.

We’ve recently been having fun with a board game I’ve developed. It’s a bit like a Monopoly board, but with only thirty squares arranged around the perimeter of a square board, numbered 1 – 30. The squares don’t represent properties, as in Monopoly, they represent punishments that Robert will receive. I do tend to overcomplicate things, so the game is quite involved, but I’ll describe a simplified version here:

The various punishments are arranged in groups of 3-6 squares each. These might be:

SP = An over the knee hand spanking
C1 = A sound caning of 24 strokes
C2 = A sound caning of 36 strokes
T1 = A sound tawsing of 24 strokes
T2 = A sound tawsing of 36 strokes
L = List, where I get to choose a punishment from a list of 10 imaginative punishments I have dreamed up Here’s a sample of just two from the list:

1. SELECT THREE IMPLEMENTS. Toss a dice to decide the total umber of strokes to be administered:

1 – 4 = 24
5 = 30
6 = 36

Toss a dice to decide which implement to begin with, then toss a dice to decide the number of strokes. Toss a dice to decide which of the two remaining implements should be used next. Toss a dice twice, adding together, to decide the number of strokes. Use the final implement to administer the balance.

2. A TIMED CANING OR TAWSING. Toss a dice to decide which implement, then toss a dice for the time:

1-2 = 30secs.  3-4 = 45secs.  5 – 6 = 1min.

Punishment to be administered briskly and hard, with no pauses.

All punishments, apart from the spanking, are administered while Robert is secured over my whipping bench, and are administered the only way I know how – with vigour.

In it’s simplified version, Robert sets off from square one, around the board with his lucky  (or not so lucky) token, moving in accordance with throws of a dice. He gets ten throws. He receives the punishment shown on the square he finishes on. He’ll be hoping for that to be SP. I’ll be hoping for something more interesting.

One final detail, is that one numbered square of the thirty will be deemed a black square. It’s a secret square between 1 and 30, known only to me. I write the number on a piece of paper together with details a very severe secret punishment (something like a 2 minute timed tawsing – Robert dreads these more than anything). This piece of paper is sealed in an envelope, then placed next the board game. If the square that Robert’s lucky token proves to be not quite so lucky, and he finishes up on the square number that I have in the sealed envelope, then he is in real trouble. But this will not be revealed to him until he is safely strapped down over the whipping bench (otherwise I might have trouble persuading him to go over it). I will take great delight in opening the envelope to inform him of his bad luck once he is at my mercy.

We’ve played this game about half a dozen times now, and each time I seem to find spiteful refinements to add to it. Robert has been lucky enough to get away with a simple spanking just once, on the other occasions he’s gone over the whipping bench, resulting in a very sore bottom.

He surprised me very pleasantly the last occasion we played. He Finished off on a square that earned him 24 strokes with the cane, and, of course, once he was safely strapped down over the whipping bench, I administered them with my usual enthusiasm. Can you imagine my delight when, having asked him to thank me for his punishment, he actually said that he thought 24 strokes hadn’t been enough?  I’ll leave it to your imagination as to how I responded.

He has, however, so far managed to avoid the black square. His luck will eventually run out, in which case I will be delighted to treat him to something that will have him struggling so desperately that he will have the joints in the whipping bench creaking. What a delicious prospect!


About Annie Bee Books

I am an author of BDSM fantasy stories.
This entry was posted in BDSM, Corporal punishment, Punishment, Spanking, Uncategorized and tagged , , , , , , , , , , , , , , , . Bookmark the permalink.


  1. SPL says:

    Thanks posting another game. I have converted almost every game on your site for our own purposes and they have inspired a few others we have been enjoying. For this one, i want to make sure I understand the board. Is the following layout correct:

    And then your list is whatever predetermined list you had created before hand for the L spots. One random spot is noted by you beforehand as the black square. I think that is very clear. I’ll have to add this one into our rotation. Thanks, again!

    • Your board is almost the same as the one we use, although yours is neater. I do tend to group punishments together, so squares 1,2 & 3 might be C1, squares 4 & 5 might be SP, and so on. Otherwise you’ve understood what we do.

      We also add a few ‘chance’ squares, where the player has to pick up cards from a face down shuffled pack of normal playing cards when he lands on it. The cards will have predetermined values. For example a RED ACE might instruct me to double the number of strokes of the next punishment. I’ve added other refinements, but I thought it would be too complicated to put in my blog.

      I’m so pleased you enjoy my games. Have fun!


      • SPL says:

        Thanks for the reply. As I’ve ‘fine-tuned’ them to fit our style, I definitely have the tendency to add much complexity. I appreciate the added details. That makes a lot of sense. I’m thinking about adding in increments before the end like administer strokes for the number landed every 3rd role (always be between 1 and 30 strokes) which would just add another layer of variance and could mean a very sore bottom. Thanks, again.

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