Wednesday, September 14, 2011

Prostate Milking

Neither Barry nor I slept well last night.  He was extremely restless and kept waking me up with his tossing and turning.  He feels it was do to being locked up for so long (it has been well over a week and I have told him that he will not have any pleasure until at least Saturday night).  I don't plan to change that decision. 

Since I made the decision to keep Barry in chastity, I have been reading a good bit about prostate milking.  I am quite intrigued about this process, and am wondering if it would be a good way to relieve sexual stress without providing any pleasure. Do any readers have experience or advice for me in this area?  Has anyone used any of the insertible devices that purportedly assist in this endeavor?



  1. Have you considered making him mastebate prior to an immediate and very hard spanking? It will soon stop being a pleasure for him because he will learn that the spanking hurts considerably much more after he climaxes, and as the mastebating is only to allow for that, he will not enjoy that much either. It takes all the 'fun' out of both.

  2. I don’t know if it’s considered milking but for two particular “ sins” my wife makes me masturbate standing in front of her and if I don’t come fast enough to suit her, she inserts a lubed finger in my bottom and I always explode. Scally is right. The spanking after that is pure punishment and something any man in his right mind tries to avoid again.

  3. Mrs. Haversackers has tried a few milking techniques to give my poor balls some relief during longer periods of denial (I'm at 60 days today), but while we can get to the point where I expel a few drops of seminal fluid, we've not been able to call it a true milking. It's harder than you think it might be.

    She has since changed to giving me the occasional ruined orgasm, which is much easier for her. She simply strokes me until I just start to ejaculate, then simply lets go of my erection. My body strains to push semen out in the usual fashion, but can't, and my come just dribbles out of me weakly. It's very frustrating and not satisfying at all, and is a very good way to drain a chaste man's bass without giving him any enjoyment.

    You should give it a try. Do it without tell Barry what you are doing. He will get very excited when he believes he is about get a pleasurable hand job, and will be quite disappointed when he doesn't get the orgasm he expects.


  4. Thank you for the various comments and suggestions.

    Scally: Early in our journey, especially when I was not as comfortable administering a sound punishment spanking, I did make Barry masturbate before being spanked. I have also used my Hitachi wand to bring him to climax very quickly; and most recently, I used our Sonicare electric toothbrush on the glans of his penis. That was very interesting. It was not as fast as the Hitachi, but its intensity was very uncomfortable for Barry. We also agree that a spanking after orgasm is extremely intense and effective.

    Harry: You make me feel better about not being able to milk any semen from Barry by massaging is prostate. However, I'm not going to give up on that idea. I have also ruined one of his orgasms a while ago and may need to revert to that as a way of relieving some stress in between more pleasant times :-).

    I am also planning to experiment more with extensive periods of teasing and denial (with the emphasis on ultimate denial after the teasing).


  5. Have you experimented with butt plugs at all.
    (Ps, did you get my email re the question for your B&B friend?)

  6. Hi Susan:

    This is Deirdre, from my blog "Spanking my husband." (I have been off blogging for a few months, but I am back, at least for the moment.)

    Regarding prostate milking, Evan and I have a lot of experience with this topic. We tried it several times years ago, with no success. I would prod and poke near his prostate, but nothing happened. (There are probably large individual differences across people for how easy / hard prostate milking may be to accomplish.)

    Then we finally succeeded, a few years ago. And now I know how to do it successfully every time, at least for Evan. So don't give up! I think the key element in getting the prostate milking to work is that there has to be a lot of semen backup. When it worked for us the first time, Evan hadn't come at all in 3 weeks. I had teased him a lot, but I had always stopped when he got close to orgasm. My cue to stopping is pre-cum: if there is any sign of pre-cum, then I would always stop then, and not continue teasing at all (too dangerous to lose any semen).

    Then we just kept trying prostate massage, with a pretty big dildo. Eventually, something happened. When it was happening, Evan said he felt something very strange going on inside him (like nothing he had felt before), and him cum started dribbling out. It came out in big drops, and kept coming out for a few minutes, as long as I massaged his prostate.

    According to Evan, it's nothing like an orgasm: he doesn't need to be hard at all, and it doesn't give him the relief of an orgasm. I guess it just drains an overflow area of semen. Evan still feels very horny even right after it's been done. So this is a good way to relieve tension in his balls without allowing an orgasm. If one was so inclined, there would be no need to take the penis out of a chastity device to do this. (We don't use chastity devices ourselves, because they make it very difficult for Evan to sleep.)

    If you want to see some examples of prostate milking, go on xtube, and search for prostate milking. Don't give up: it really does work in the way that others have written about on the internet -- a steady sequence of drops of semen, with no erection necessary -- if one does it right. For Evan, a successful milking session is based mostly on the time since the last ejaculation. The longer that it has been, the more successful the milking: the greater volume I can milk from him.

    Good luck,


  7. Thank you Deirdre for the thorough explanation of what has made a difference for you and Evan. And, for giving me encouragement. I plan to continue trying, especially after Barry has been orgasm free for a longer period of time.

    Also, I'm glad to see you back blogging again. You've been missed.


  8. My wife does not allow me an orgasm until I have been in chastity a full 6 weeks. And then additional weeks are added for poor housework or attitude, or because she feels like it. So 2 months or better is when I can cum. My wife feels that 5 to 8 orgasms a year are more than enough for any man. She favors the lesser amount. So this guy is whining after 1 week? Oh boy, make him wait 6 weeks!!!

  9. guys is right make him masterbate before a spanking ,or that makes the spanking hurt so bad, a nice dildo or strapon , will milk a guy with out being hard , it just poors out , i get to collect mine , i lick it all up . its all fun

  10. I bought a e-book and video package about prostate milking at and now can't get enough prostate pleasure, it is fantastic!

  11. I agree with Deirdre. It took a while to figure it out, but once I did, wow, it was amazing. I had no idea my boyfriend could possibly have so much dribble stored up in those little balls of his! The trick is, as Deirdre said, he has to have a good amount of semen build up, a few weeks worth at least. We don't yet practice male chastity, but that's next on the "to try" list.

    I found the following website useful as far as tips and techniques:

  12. My wife and I used a prostate massager. I too and kept locked up and at her decision she brings out the massager and uses it on me. I am locked up and can't get an erection but I have a "full body" orgasm which is earth shatttering for me.

    I expell a great deal of seminal fluid and at times some actual cum. This is how I get releif now, I kind of forget how a male orgasm used to feel.

  13. I haven't been put in chastity yet although the concept has been discussed briefly. I am however a spanked husband. There is no doubt that a spanking after a climax hurts way more than one prior. Either way I become very obedient after a spanking or after I am told to lick.

    Spanking and firmly guided oral make most men submissive and if you don't allow him to orgasm he will remain submissive till he is finally given relief.