Keyholder Thoughts: Orgasm Denial and Chastity

Cagedmonkey and I just finished up an almost 3 month period of denial, 80 days to be exact. It really pushed the limits for both of us because it was the longest we had taken the denial with some pretty intense teasing along the way. Since putting cagedmonkey back in his Jail Bird, I’ve been trying to decide how to handle his next denial period. I figured it might be a good idea to come to the blog and get out my Keyholder thoughts. Perhaps some of you have thoughts or ideas you’d like to mention.

Since we’ve done a bunch of different periods of denial already I don’t see denying him until Christmas or New Year’s (6 months) being a real issue. So I’m leaning on that being the actual denial period but along the way I love to throw in some intense teases, hardcore frustration and those lovely things to endure. I’ve thought about certain time periods of complete 24/7 wear with zero time out for even an erection. It would have to be a month or longer for this to be a challenge for him. I was also thinking that part of that, or another period itself, could be him wearing the Revenge and doing a “no look, no touch” thing for a couple weeks to a month.

I am loving the idea of a progression thing that goes along with the 12 Days of Christmas. Ideas are anything from just stroking him each day for longer and longer to actually doing a new, added thing each day. Like, a butt plug the first day and then the second day would be two nipple clamps and a butt plug and third day could be 3 stokes, 2 nipple clamps and a butt plug… etc but that would be twelve ideas I’d have to come up with! I could do a new thing added up to five and then from there could be spankings… hmmm.

Ok anyway, you see my thought process here. You know I love to keep things interesting so I’m kinds curious what others think of this. Would you like your Keyholder to do something like this? Something different, what? Something more? Something less? Would you like to see me put cagedmonkey through something in particular that I have or maybe haven’t done already? Let me know!

I hope to hear you’re thoughts!

5 responses to “Keyholder Thoughts: Orgasm Denial and Chastity

  1. Instead of letting have a cum fest, you would start with a certain amount of time and make sure he cums even when he feels done. For example, cum 3 times, which is possible and on edge of an over load, then after the three times, for every orgasm, he will have 1 month subtracted from a 12 month sentence. The first three are possible, after that, you have to have a really good imagination, porn and the will to keep cuming. Any male here ever come more than 3 times in say, a 6 hour period? How about 3 hours šŸ˜‰


    • I’ve gotten cagedmonkey to cum more than 3 times in a few hours… but like once! šŸ™‚ haha most of the time on a break from chastity I’ll get him like 4 times a day. Mmmmmm


      • It is hard to do. I have cum 3 times in one session. During the third time, the erection is very full, Almost painful, but a good pain, After that, it’s just hard with no orgasm. A good way to get that full blown hard one without him cumming. Hint! Great time to get yours’


  2. Sometimes it’s hard to think of games to play with chastity to keep things interesting and new. Lots of people play card games and roll dice. My KH sometimes does forced orgasms. She has had me do four in a row with just a minute or so rest in between. They get kinda painful and really make you not want one for a while.
    So here is an idea. SPOILER ALERT!!! The rest should be a suprise.
    Have him orgasm as many times as possible in a set amount of time. Then let each orgasm equal a certain amount of time in chastity. For instance, you give him two hours and he has seven orgasms. An orgasm is two weeks in chastity, so 14 weeks locked. But don’t tell him until after the cumfest. Hope this gives you some ideas.


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