The back-story-setup is like this: He’s in chastity (physical or honour system – either one is fine). He’s not allowed to pleasure himself other than under your expert supervision.
There’s two variations of this challenge: Either it’s him masturbating, or it’s you doing it for him. Naturally you doing it for him will make his mind go wilder and thus make the challenge harder (see what I did there?) for him to complete. Either way, whether he does the stroking or you – it’s up to you to make it more difficult for him by adding lube – perhaps the kind that tingles or the kind that warms his member, whatever you’d like to try.
You start on Day 1 by tell him that Rule #1 is that he’s allowed 100 strokes – supervised! Nothing more! But also, nothing less! (that last bit is important). You then proceed with either him stroking himself or you doing it for him. 100 isn’t so hard, really… you’d be surprised how fast you go through 100 strokes – especially if his penis isn’t hard yet when you start (remember, he’s not allowed to stroke it before to get it hard, that’s cheating!). Day one is naturally rather frustrating and he’ll likely think: “WTF”
Day 2: You tell him that today he gets 100 x 2 (100 times the days). Again, nothing more than this 200, and importantly nothing less!
Day 3: 100 x 3 = 300
Day 4: 400 strokes. You get the picture. Naturally the more strokes he (or you) have to do, the closer he’ll get to cumming and the harder it is going to be for him to go all the way with all 400 strokes in one go. This is where Rule #2 comes into play: He’s allowed to take as many breaks as you, his mistress allows. That way you can stroke him say 30 times and if he needs to take a break every 30 or so strokes that’s fine! It’s generally a good idea to give him unlimited breaks. You might think: “Wow, if I give him unlimited breaks we’ll be at this all week!”.
That’s where Rule #3 comes in: All the strokes has to be done before midnight of the day! If they’re not done, you start with X = 1, thus you start back on Day 1 again with 100 strokes!
And finally, Rule #4 simply states that if he orgasms, even if you ruin it (which you should!), you start at Day 1 again!
The goal of the game? Well now, how does 1000 strokes sound? Yes, that’s 10 days. Or perhaps 2000? 3000? Or even see just how long he can go without a proper orgasm! Believe you me, he’ll be getting hornier and hornier, so 100 strokes on Day 10 means a whole lot different than the same 100 strokes he got on Day 1!!!
Have fun ladies!
PS: Oh, and X doesn’t need to count up in increments of 1 you know!