Strange Predicament

Discussion in 'Chastity and orgasm denial' started by Hoss, Sep 23, 2008.

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  1. Hoss
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    Hoss New member

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    A quick recap on my unique situation. A good friend, S_, is my key-holder, no play between us outside of the game, when she wants to release me she gives me the keys and I take care of the rest. She really doesn't care what I do as long as I don't cheat, or do anything too stupid(don't ask, but it's cost me).

    I also have a head-turning lesbian I "date" from time to time. Which works out great, because I do enjoy company when I dine occasionally, and with her I don't have to worry about having to explain my situation.

    Now for my predicament:

    Saturday, I was at a pub that I frequent for lunch. The bartender was a you lady whom I'd made a pass at a couple of months ago(yes, I was locked at the time). She shot me down, as I expected. Most of the time I flirt with women and hit on them it's for sport, at least that's what I tell myself to pretend I don't mind getting shot down.

    Back to the point, this lass asked me out. At least that's the way I read it. She had a specific idea, and I told her we could do that. She's got to figure out when her work and school schedules allow it. Thinks are a bit messed up here right now thanks to a little wind storm we had a little over a week ago(it might have made the news, not sure).

    Anyway, I know that IF we hit it off, and I wish to pursue something with her, that S_ is going to want to meet her before I get the keys. S_ has known me for years and has seen me make one tow many mistakes with my choice in women. Sure I could cut the device off, but that would violate the trust that S_ and I have, so I have no choice.

    The predicament is this, IF things go that direction, exactly how do I explain all this to the lass who asked me out? Something tells me, my usual bluntness might not be the best way.

    Course, it may not even come close to being an issue.

    Yeah, things would be a lot easier if I had a more conventional relation with my keyholder.

    It's time for me to go find Morpheous,
    Hoss
     
  2. stealth
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    stealth Senior Member

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    Interesting predicament you have. I'd probably go something along the "big sister" route. Like:

    "S_ and I have know each other for years and she's something like a big sister to me. I've mentioned you and she really wants to meet you."

    Who knows, maybe she'll leave you locked up, forcing some platonic dating to make sure the two of you are compatible. Then, at a later point she gives the key or a copy of the key to the new woman.
     
  3. Mistress Watchful
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    Mistress Watchful Dont believe the hype ;oP

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    And I don't think that would be a bad thing... I think it would drive the new girl crazy for you!
     
  4. sissyboyblue
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    sissyboyblue Member

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    yes the big like a sister thing would be best...and if S forces platonic dating for a while so much the better. S and the new lass might hit it off and talk about your chaste situation...the keys might be passed without your knowledge. Anything could happen. I hope it works out for you
     
  5. Hoss
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    Hoss New member

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    Well, I talked to S_ about it, and she is going to want to meet her before she lets me out to play.

    Part of me wants things to go that way, but a huge part of me doesn't look forward to that conversation at all. No matter if I use the "like a sister line" or come out and tell her the full story, it's going to be awkward.

    Why the hell didn't I think of that before I said yes. Maybe she'll chicken out, but the gods hate me, so probably not.
     
  6. Missy Tanya
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    Missy Tanya Senior Member

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    Dear Hoss,

    Why would S_ be upset at you finding someone to have sexual relations with. You state that your relationship with S_ is just very good friends. She seems to have nothing sexual to do with you. Does S_ expect you to never find someone to have sexual relations with again.

    Of course she doesn't have to give you the key for the first few dates. She could have you report a play-by-play breakdown of the dates. She could tease you by holding the key just maybe a couple dates too many. Then after you have shown S_ that you are not jumping into something to soon, S_ could release the key for date nights only.

    The big sister idea should work, as long as S_ doesn't give the new girl the more than sister impression. I would if "I were in your shoes" tell the new girl about S_ on the first or second date. Let her know how important S_ is in your life. Then when you suggest the meeting with S_, she should not be too surprised.

    I like other have said they may just hit it off and control you together and you will live for them, not for your known. Hell most of us would love to have to answer to two women to earn the right to cum.

    Just my thoughts, off base as they maybe, Missy Tanya
     
  7. Hoss
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    Hoss New member

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    S_ primary concern is not me getting to go play, she has just seen me make one too many bad choices when it comes to women. Including the last one that she had a ringside seat to, and from time to time would warn me about. Usually she would say something like "I support you, if this is what you want, but you're a f&%^ing idiot.

    Heck if I was the type of guy who could pull off a one night stand with ease, then she'd let me do that whenever she wanted to release me. But that's not me, I'm the type that wants something more, and she knows it. It's mainly a desire to save me from myself.

    It's kinda nice actually, having a friend that wants to save me from making those stupid mistakes, and has the ability to enforce it.

    It's about to become very real, too. I am going to upgrade to a more secure device, something that I can't cut off very easy. Once I do that, S_ will have one key, and my other best friend, T_(who has helped me test previous devices) will keep the other. So far the plan is, T_ will not be an active keyholder, more of a human safe deposit box. If S_ asks for the key, then T_ will give it to her as soon as possible. If I ask, then it'll be a minimum of 2 months, then she gets to decide when I get it, basically she be comes the keyholder. The two months delay is basically to make sure that I don't ask for it because I've pussed out.

    The back up keyholder is not because I don't trust S_, or T_ for that matter. I just don't trust the gods, they hate seem to hate me after all.

    Really, I guess I am pretty lucky. I have two women who are both good friends, both are willing to indulge me in this kink of mine. And both of them want to save me from making yet another mistake when it comes women.

    I only have one choice in the matter though, and that's just to "wheel the wild dance". See where this goes, maybe no where, maybe some place incredible.

    Hoss
     
  8. mikecb
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    mikecb Member

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    Hoss,

    If you truly love the Chastity lifestyle, then you should commit to it. I think the plan would be that S_ will hold your key until she turns it over to the next (hopefully permanent) lady in your life. If that's the way you want it to play out, then the next step with this lady (or any) would have to be that you come out to her, completely, about your chosen lifestyle. If she runs screaming, then you know it never would have worked. If she can adjust to it, then maybe she's the one.

    I think it would be amazingly hawt to date a woman for some time, with no hope of release, until the keys are finally turned over to her control. *fans self*.

    That's my two cents,
    Mike
     
  9. Hoss
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    Hoss New member

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    Mikecb,

    I actually agree, some what. With most things I am usually full exposure. Years ago a prodom asked me why I was the way I was. I told her that I believed that in order to be in harmony with the universe, one first had to be in harmony with ones self and the way the fates made you.

    I hadn't thought of that in a while. But what you said did remind me of it. If she runs, she runs. If she can't handle this, then there is no way she will be able to handle the stranger kinks of mine.
     
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