Need advice on best way to self milk please?

Discussion in 'Chastity and orgasm denial' started by Lessthan4inches, May 28, 2015.

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  1. Lessthan4inches
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    Lessthan4inches Active member

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    #1 Lessthan4inches, May 28, 2015
    Currently in CB6000S and Mistress used to allow me to masurbate to orgasm once a month. This then went down to once every 2 months and more recently she decreed that it would be just 4 times a year. That was a worrying prospect I have to admit, but a turn on too in many ways. However, Mistress has now decided that my pathetically small penis (under 4 inches when fully erect) really doesn't merit any attention and as a sign of my devotion to her she has instructed me to order a Jailbird which will then be worn 24/7 permanently, with no possibility of release.
    It must be ordered with the security screws and she will retain both keys. She even suggested that she might enjoy watching me throw the keys into the river, as it would entertain her for a few minutes. (I hope she is not serious).

    She will graciously allow me the privilege of 'self milking' purely for prostate health. Could anyone experienced in long term / permanent chastity please advise on the best way to do this, as I have tried several methods as seen on the internet with no success at all. I am worried too about the TOTAL loss of erection and orgasm. I am already partially feminised and enjoy being that way, but still enjoy playing with my little cocklet when allowed. Obviously it is certainly not my place to question my Misstress's authority, that would be unthinkable. It is a tough one though...!!!!

    So I am stuck with the prospect of permanent chastity looming on the not too distant horizon.

    Will I be able to milk myself successfully within the confines of my jailbird as it will stop my erection???

    Please help alleviate my fears and kindly give me the benefit of your wisdom fellow 'Mansioners'.
     
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  2. SamanthaCDNJ
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    SamanthaCDNJ Member

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    #2 SamanthaCDNJ, May 28, 2015
    i wear a jail bird and have been able to get release in it by shaking it or using a vibrating massager on the cage.
     
  3. Lessthan4inches
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    Lessthan4inches Active member

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    #3 Lessthan4inches, May 28, 2015
    Hi, Thanks for replying, that sounds hopeful, but are you semi erect or do you have room to reach a fully hard erection? I will be ordering a jailbird that will not have room for me to become fully hard. The CB6000S that I wear now stops me getting fully hard too. The jailbird will be slightly shorter on my Mistress's orders, she detests the thought of me getting a full erection as that would spoil her enjoyment. She really does like me being constantly limp and feminine. Even at night now I don't seem to get nocturnal erections, if I do then they must be quite weak because they don't wake me up. Are you locked up long term may I ask?
     
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  4. SamanthaCDNJ
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    SamanthaCDNJ Member

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    #4 SamanthaCDNJ, May 28, 2015
    not fully hard at all. i AM fully straining against my cage but even that can be controlled, just don't exert at all while doing it and the sensations of moving the cage or the vibrator takes over. I find the build up is pleasurable but the release is not, its unsatisfying in the end.

    My Jail Bird is tight as well with little room for expansion
     
  5. harddenial
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    harddenial Member

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    #5 harddenial, May 28, 2015
    An Njoy pure wand (large end) does the job. You will find other recommendations for it on this site and elsewhere. Nothing else has worked for me.
     
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  6. Lessthan4inches
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    Lessthan4inches Active member

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    #6 Lessthan4inches, May 28, 2015
    Thanks for your advice, I think I will have to experiment once I get my Jailbird as I don't know what to expect in the meantime. I do think a vibrator might do the job although I was considering a prostate massager. I bought one that was a waste of time, maybe something larger needed and more practice.
     
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  7. Lessthan4inches
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    Lessthan4inches Active member

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    #7 Lessthan4inches, May 28, 2015
    I have tried similar in my CB6000S but can't quite 'get there' almost but can't hit the trigger point. I am used to spoiled orgasms as that is all I have been allowed for over 5 years...!!! ( I have cheated a few times and gone full blast, but then I feel guilty afterwards.) I have very mixed feelings about 24/7 indefinite chastity, but I will just have to deal with it I guess. My Mistress is just exerting her will over me and it does please me knowing that she is enjoying such extreme control. Her satisfaction is the only thing that matters obviously, I am just a servant and nothing more.
     
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  8. Wendygirl
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    Wendygirl To offer advice and keep CM safe and welcoming

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    #8 Wendygirl, May 28, 2015
    Milking is definitely a practice thing and just finding what works for you.
    Something curved or say a realistic dildoes with a nice fat head might work.

    An erection is not necessary or often not possible but just relax and practice and have a look at anatomy pictures and diagrams.
    Xx Wendy
     
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  9. guest 2942
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    guest 2942 Long term member

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    #9 guest 2942, May 28, 2015
    x2 for njoy pure wand
     
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  10. Lessthan4inches
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    Lessthan4inches Active member

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    #10 Lessthan4inches, May 29, 2015
     
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  11. Lessthan4inches
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    Lessthan4inches Active member

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    #11 Lessthan4inches, May 29, 2015
    Thanks for your advice, I think my prostate is further in than normal. I have used all kinds of anal toys over the years, big and small and they are great fun but I have never experieced hitting the 'p-spot' I was generally using straight dildoes and butt plugs (some 2" diameter) when, as you say, curved toys would be better. I will keep trying out of necessity. Thank you so much for replying. X
     
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  12. Lessthan4inches
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    Lessthan4inches Active member

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    #12 Lessthan4inches, May 29, 2015
    Thanks for endorsing the wand suggested above. I will check it out and probably get one. I appreciate your reply.
     
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  13. seasoned
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    seasoned Long term member

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    #13 seasoned, May 29, 2015
    Found this somewhere;) and thought it appropriate:

    For me it's a willy,but he calls it a cock.
    It's no use to me so let's take stock.
    I can't feel when it's in,so would it be a sin
    To neuter him with a cage and a lock?
     
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  14. Lessthan4inches
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    Lessthan4inches Active member

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    #14 Lessthan4inches, May 29, 2015
    Yes, most appropriate and it is effectively neutering or, as I like to think of it, total immasculation...!!! Thanks for sharing this/
     
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  15. N23orMore
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    N23orMore Long term member

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    #15 N23orMore, May 29, 2015
    I love my NJoy Wand but sliding Jeff Stryker dildo up inside will release my fluids also.
     
  16. billie1
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    billie1 Active member

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    #16 billie1, May 29, 2015
    Have you tied estim, I have been in a mm jailbird for a couple of years now, and mainly get milked with this. Mistress always turns it up when I start to leak, so only pleasurable if you are a masochist! ( which I am)
     
  17. N23orMore
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    N23orMore Long term member

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    #17 N23orMore, May 30, 2015
    Love the feeling of estim.. Have a ET-312 machine. Do some reading on the Smartstim.com board if you want. There is nothing like building up to a huge hands free orgasm (HFO). And not just milking, which you can do, but a full orgasm.
     
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  18. Lockedbytrace
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    Lockedbytrace Intense feeling atm.....

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    #18 Lockedbytrace, May 30, 2015
    My skills at self milking are getting pretty good since my chastity adventure started. My kh loves watching me use toys to make my caged cock...sorry her caged cock ooze without stimulation. I recomend a video on porn hub I'm not sure the name but it's a tutorial about giving your man a prostate orgasm and it's a 40ish yo lady talking u through how to use a prostate toy. That helped me accept its ok to enjoy prostate play its actualy normal!
     
  19. Luscious-Liza
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    Luscious-Liza Liza

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    #19 Luscious-Liza, Jun 1, 2015
    My wife/mistress has trained me to climax with anal stimulating my self only ...I find what helps me is my njoy eleven ...
    I Must say having a anal Orgasm
    Is something.
    Much stronger , from deep inside having my princess watch me how I'm pleasuring my self to climax is something. ..
    She calls it my women's orgasm
     
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  20. Waterluv
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    Waterluv Sissy Lesbian Renee...

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    #20 Waterluv, Jun 2, 2015
    Estim is awesome. Had some of the most earth shattering hands free orgasms! Felt like my mind was separating from my body! Don't know if I over did things? Used pads on the genital region, and a prostate probe. Had three negative side effects. Experienced some permanent desensitized areas, became more challenging to orgasm with prolonged use, and got "buzzy head" (kind of a 30 minute after effect similar to having too much alcohol to drink). Keep in mind everyone will have a different experience with this! Always be safe! Unfortunately, I had to get rid of my Tens unit. Never tried it with chastity, but it would have been a blast :)
     
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  21. Waterluv
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    Waterluv Sissy Lesbian Renee...

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    #21 Waterluv, Jun 2, 2015
    You're living my fantasy lockedup66! I'd love to be told the only way I'd ever orgasm again is by my mistress strap on, putting a hitachi wand on my cage, or rubbing myself off with one finger like the bitch that I am! LOL! Womens orgasms rock!
     
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  22. Luscious-Liza
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    Luscious-Liza Liza

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    #22 Luscious-Liza, Jun 2, 2015
    Being forced into all this is probably the best way. ..my princess is having me experience feelings that a woman feels having an orgasm like a woman has....
    I must say it is amazing!!!
    ..to have her work me over talking me though it ,,relaxing me to be able to climax with anal stimulation is something else. .
    The first time I screamed out so loud it might of been the strongest orgasm I've ever had
     
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  23. Lessthan4inches
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    Lessthan4inches Active member

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    #23 Lessthan4inches, Jun 2, 2015
    Your experience has made my mind up on the best way for me to milk myself. If I fail at least I will have fun trying. I don't expect to get it right first time. Thanks for your contributions to my thread. X
     
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  24. Luscious-Liza
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    Luscious-Liza Liza

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    #24 Luscious-Liza, Jun 3, 2015
    Hi.
    I hope you're experience is as good as mine. :)
    I have to thank my beautiful princess/wife/ Mistress for having me experience these feelings.
    Like I said before it took a lot of help from my princess helping me through this. ..
    but I must say what a great feeling what a experience, ,,
    I hope you enjoy your self and bring your self to the greatest feeling you'll ever have like me.
    it took my Mistress some time having me relaxing and excepting what I was enjoying. ..
    but let me tell you when it happened it changed me for ever ....
    please keep me posted on your experience :)
     
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  25. Lessthan4inches
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    Lessthan4inches Active member

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    #25 Lessthan4inches, Jun 3, 2015
    Thankyou. I will certainly update you. I have lots of experience with anal toys and from anal sex (I am bi sissie male) but no experience in routine milking. We are now mutually 'following' each other.(Thanks)

    Hugs. Angela. X (aka lessthan4inches)
     
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