To celebrate our anniversary this weekend, My Lady and I are taking a trip to a local casino for some gambling & drinking fun. She even set us up with a babysitter for the day so we can go and enjoy ourselves without the kids in tow. What a wonderful anniversary gift for BOTH of us!

Until, of course, I open my big mouth.

You see, part of our agreement is that I tell ML about any and all fantasies or ideas that I get that involve our sex life. ML has been struggling with the decision on whether or not to let me cum on our anniversary – she REALLY wants me to fill her up with a nice hot load of cum, but she also REALLY wants to push me further. She couldn’t decide. That’s when my kinky, creative brain kicked in and came up with an idea that she seems to like a helluva lot more than I probably will.

Here’s my idea – we are going to find the roulette table in the casino and choose one spin to dictate a number. That number will determine how many extra days will be added to my current stint of orgasm denial. Thanks to the zero and double zero spaces, I actually have a 1/19 (~5%) chance to cum that night. However, I also risk the possibility of having to go another thirty six days without an orgasm. Considering I am already approaching three weeks without an orgasm, the longest time since we’ve started our chastity lifestyle without cumming, adding another month-plus on the back end is going to be torture. I know what I’m rooting for. What My Lady is hoping for is a mystery to me…

Wish me luck!