Is milking yourself considered cheating?

Discussion in 'Chastity and orgasm denial' started by Consumed, Jun 11, 2020.

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  1. Consumed
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    Consumed Right where I belong.

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    My wife and I have a contract and it doesn't specify me milking myself..... just that it must be done once or twice a month minimum.

    I have only done it a few times before but last night on only day 3 into my lock-up, I used the wife's strap-on dildo. I was still horny afterwards like normal and didn't feel like it scratched the itch fully but boy did the cage fill up with. (I swear milking produces way more cum)

    My question is, do you think it's considered cheating if I did it without her knowing? I'd like to think a full-blown normal orgasm with penile stimulation is what really counts because it's a true release. IDK I just feel a little bit guilty, not too much tho
     
  2. Peaches
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    Peaches "kinky guy"

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    What would her reaction be if she caught you in the act?

    If you have to sneak around to do it then it's cheating.
     
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  3. MissyB
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    MissyB Long term member

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    If she gave your orders to be milked monthly and afterwards you don't feel fully satisfied by your discharges, then it would seem to be fine. Personally, I wouldn't want to bother my Mistress every time i needed a milking. Going forward, you might just inform her you are meeting her requirement in case she's interested in observing. To be safe, ask her for guidance.
     
  4. DonnaSue
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    DonnaSue Long term member

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    In our relationship, anything I do to myself that causes me to enjoy anything without her involvement, is considered cheating. But, if She specified that you are to be milked a certain number of times, either She would be agreeing to do that or it is tacit permission for you to carry out Her wishes, it would seem. Does She ever milk you?
     
  5. King Hippo
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    King Hippo Long term member

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    I would imagine there must be something in your agreement that says....

    "Any sexual activity is dictated by the Keyholder..."

    I would consider this sexual activity... I would talk to your Keyholder about it...
     
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  6. Isopropylforyou
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    Isopropylforyou Long term member

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    If it is without her knowledge then yes your cheating. This a lie by omission. You are not telling her. You are not being the best you can be. Tell her now. The longer you wait the more damage you will do.

    Mistakes happen, it is a part of learning. How you handle your mistakes makes all the difference.
     
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  7. Guest 2684
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    Guest 2684 Long term member

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    Yes I would say cheating she was not involved or you were not given specific instructions to do so you should tell your KH
     
  8. Consumed
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    Consumed Right where I belong.

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    Thanks for the replys everyone. I asked for clarification in the agreement #9 His pleasure is solely at her discretion and may be in the form of by hand, vibrator (locked or unlocked), anal only, or vaginal. A minimum of once per month....

    She says it needs to be supervised so whether it was a misunderstanding (it's our first contract) or a rule broken we shall see.
     
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  9. tomf_22033
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    tomf_22033 Long term member

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    it doesn't matter what we think. Discuss it with her.
     
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  10. Peter Rabbit
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    Peter Rabbit I'm her bunny

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    Tell her. Keep it fun and light. She can decide if it’s cheating.

    For us, in 2017 she decided that all forms of play without her were forbidden. It ramped up to even fondling my balls while locked. That was a real struggle.

    We took a step back this year because things got too hard for me. I can play with butt toys now and have been keeping myself plugged. I can milk myself if I want to. I just haven’t yet. I’ve just kept myself squirmy with a plug inside me.

    But this was all up to her.
    It’s better this way.
     
  11. Rectrix
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    Rectrix Long term member

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    So you have your answer -' "it needs to be supervised." But you knew that. You're in chastity for a reason, and the prime directive is she controls any release of your semen. What you call private milking (after only 3 days, no less) is just anal masturbation.
     
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  12. Disciplined Boyfriend
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    In my own relationship it would be wrong - that's the way our rules work.

    If you feel guilt then you very likely to have done something that breaches the trust you have with her. Time to 'fess up and face the consequences or do nothing and ask her the rhetorical question "Would it be bad if...."
     
  13. sandman9355
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    sandman9355 Junior Member

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    I'll add my voice to those telling you to talk to her. If you're too worried she might be unjustifiably angry, begin with asking her about you milking yourself in the future.

    Edit: I forgot to mention I'm not even sure the rule you've mentioned applies. Is the milking actually a pleasure?
     
  14. Consumed
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    Consumed Right where I belong.

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    I asked her about it and yeah she said it needed to be supervised.
    She considers it a pleasure act. It's definitely nice to me but also a bit of torture too because I'm still horny afterwards.
     
  15. madams-sissysub
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    My madam allows it I just have to ask permission first, she finds the sight of me pumping away at my self highly amusing!
     
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  16. starflyer
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    starflyer Junior Member

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    yes I would say its cheating
     
  17. b_quark
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    b_quark Long term member

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    It really depends on your KH. I know my wife does not allow any milking or ruined orgasms without her explicit permission. She has at times allowed me to massage my prostate with a vibrator or ride my dildo to have anal orgasms, but not often, usually when I have been locked for several weeks. She has even been upset when I have accidentally cum in my cage from being so aroused watching her orgasms.
     
  18. fkfk
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    fkfk Active member

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    If you have done anything to yourself without your KH knowing nor acknowledgement, it is cheating.
     
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