A Fun Masturbation Game I’ve Done With Jack

We usually play this game after a couple of days or maybe a week without him cumming.  We start with a long teasing session, in which he gives me pleasure and all the orgasms I can handle.

Then we start by putting a non-lubricated condom on his throbbing and already near the edge cock.

The Masturbation Game

We then take turns stroking his cock for a pre-determined number of strokes.  We start at 10 and increasing by 1 every round until we get to 25.

This is quite a lot of stroking for a sub denied for a couple of days and after being put on the edge. Of course, you and your Mistress can always change it up – start at 5 if you’re a minute man, or go to 50 if you have stamina.

Anyway, I give him 10, and then he gets to stroke for 10, then we go to 11 and so on.  His goal is to cum while he’s stroking his cock, and mine is to coerce an orgasm out of him while I’m stroking it.

He has to count the strokes out loud to make sure there’s no cheating!

Winning The Masturbation Game

If Jack starts to cum while I’ve got him in hand, I get to choose whether to stop and ruin his orgasm or continue to drain his balls.

I’m sure you can guess what I almost always choose!  He lost, he shouldn’t enjoy it!  Then, I carefully slide the condom off and have him eat his cum for me

If Jack starts to cum while he’s stroking?  Well, he gets to complete his strokes.  So if he starts cumming at stroke 11 of round 16, he has 5 strokes left to complete his orgasm. Once he gets to 16, I take his hand away from his spasming dick.

He doesn’t have to swallow, but that slut always does!  If he makes it to the last round without cumming, well then he’s denied.  Obviously, he hasn’t been in chastity long enough!