Milking Your Prostate
After you have been in chastity for a length of time, your chastity Mistress may decide it is time for a release. This doesn’t necessarily mean you will get to have an orgasm. There are several ways she can provide a release of built up semen without providing the pleasure of an orgasm. One of those ways is for your Mistress to milk your prostate. Now, naturally, if you are in chastity training with a phone sex Mistress you will have to follow her instructions very carefully and milk your own prostate. It’s a very simple procedure. Keep in mind that milking your prostate helps to maintain good prostate health, also. If you discuss it and plan ahead, an aneros can be quite beneficial in the milking process. If not, use your finger and some lube. You will need to insert it anally and locate your prostate. You’ll know when you find it, because it will be pleasurable. You will be instructed to rub your finger against your prostate until ejaculation occurs. At no time are you to stimulate your penis in any way. Thus, the release of semen but not the pleasure of an orgasm. It’s healthy to do this at least once a month during chastity. But, it’s always up to your chastity Mistress, of course.
Ruined Orgasms
Some chastity Mistresses prefer the ruined orgasm. I’ve spoken about this before in previous posts. The ruined orgasm is similar to a prostate milking in the fact that you don’t derive pleasure from the process. However, you will be allowed to stimulate your penis. You will be allowed to masturbate, although your Mistress will most likely give you very specific instructions on how she wants you to masturbate. At the crucial moment of orgasm, you will be instructed to completely take away all stimulation, thus leaving your penis to pump and spurt and complete the ejaculation all by itself. This will be frustrating, to say the least. I guarantee you that this method is not for the easily tempted.
No matter what methods you and your chastity Mistress decide on together, your journey to chastity will certainly be fun and interesting!




The more I read and see ruined orgasms, the more I am interested in trying it. Obviously this needs to be worked out with my Mistress Tia before hand. To feel such despair as the weeks or even months of tease and denial…and perhaps all that time She has instructed and guided you through so many frustrating edge sessions only to deny you….then to be taken just half a stroke over the limit and ordered to stop stroking…then the agony of the ejaculation without the orgasm. I want to try it (I think). It gets me so hot to give myself to Her that way.
You describe a ruined orgasm so perfectly, pet. I can’t wait to experience one with you! Valentine’s day isn’t far away.