Talking a girl into becoming keyholder? Any suggestions?

Hi all,

I'm currently self-locked for 2 weeks at the moment. I got serious about chastity as a way to combat my masturbation habit (especially at nights), although the psychological and SM aspects I find quite appealing. My excessive masturbation I believe contributed to ruin several relationships, I simply was not attentive enough, my abilities in bed plumetted too, i was at times even unable to cum during sex at moments which always disappointed the ladies. Add to that laziness and countless hours spent watching porn (even while in couple) and you got the recipe for disaster. It was big time to get rid of that addiction, and it already works.

Now about the lady in question: it seems that we are about to resume relationship with a girl, that we had to end a couple years ago. What's more is that she is actually almost a natural-born dominant! I didn't think about that as I was starting out, but now I thought she would be the perfect candidate if things work out.

While we were together she was kind of authoritarian, but in a gentle way, made me do things for her (something that was usually rewarded, especially when I didn't ask for), but probably dissatisfied with our sex life. Here we come back to that mastubation problem mentioned in the beginning. She did enjoy the oral and the massages though and I gave her plenty of those. So she started seeing other guys at some point, first discreetly ("I'm so busy, can you take care of this and that please") then almost openly - not saying this directly but suggesting in no uncertain terms she had been serviced by someone. Finally we even ended up in a bigamous relationship, where she was seeing another sub, without neither hiding it nor advertising (but all her friends knew). She at the same time keep things smooth - neither of us felt humiliated at any moment, she separated her time with us both quite well, though we did meet occassionnaly.

But, what's most interesting she had no clue about BDSM - knew nothing about terms and definitions of things and could not care less, although we were in a cuckold relationship, and with a lot of tease and denial too. She had an outsider's view of SM, like just handcuffs and whips, I knew a bit more, but without investigating that seriously.

However, recently we resumed contact, ther was mutual interest in seeing each other again, she even made me some gifts. Recently we went to an event together, and after while talking in a bar we laughet a lot and talked, including about sex. She was clearly flirting with me. One more thing: one of the guys she dated recently was a pseudo Dom (which turned out to be false she said), but she now knows quite a lot about BDSM, as he introduced her to that. She told she's been at some parties, fetish and swinger, but didn't want to have any sex or play there, not liking the atmosphere, all the drooling guys etc., but clearly I see some interest in the subject. Basically she's a natural psychological dominant.

So I thought, if things work out between us this time, what if I tried to turn her my keyholder? Of course I'm not about handing her the key outof the blue - she would freak out, but she probably knows about chastity too (and she already practiced teas and denial before having any BDSM awareness .
What I was thinking to do, is to try to propose her a massage when the occasion comes by, turn it into a 69, and, as she likes to blow with her hand when she sees my load which I believe would be pretty big, given my chastity time, and that's where I'd casually mention that I'm trying to refrain from masturbation and how hard it is with pure willpower and so on. If she does not offer to get a chastity cage straight away (which may happen, although I am not planning to show mine at this time, not right away in any case), I think the seed will already be planted in her mind? I'd even pretend to disagree a bit, to make her more interested.
What do you think?
Best regards,
D.

 

Thanks, that's exactly what I'm trying to avoid, hence searching for advice This is why I thought to suggest it to her from that "curing masturbation" angle (which is mostly true anyway, and see what happens.

That said some planning ahead (or even plotting) is needed I guess

 

No, no, that's just a pretext to tell the masturbation story, and only one idea how to do that. That can happen over a coffee if the discussion goes in that direction, although after some sexual activity it'd be simply more natural.
Then once the subject launched, and as we may come back to it later I hope one thing leads to another...