Dating and chastity advice

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wishful4
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Re: Dating and chastity advice

Post by wishful4 »

This is one thread where we could use the wisdom of our Keyholder members. Their perspective could be helpful and enlightening. What say ye, Keyholders?
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Wishful4
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TwistedMister
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Re: Dating and chastity advice

Post by TwistedMister »

belocked wrote: Thu Apr 08, 2021 12:30 pm
I should add that she's a pretty confident person and I thought she would be interested. Maybe it's just going to be a game, maybe it will be more than I'm ready for, but I'm game for anything at this point. I have a dermatologist appointment later this month so I know I'll be out for that, and she's not (yet) ready to take the keys so it's really up to me for now. But I can see the look in her eyes that tells me she may really take charge.
Sounds like you're on the right track, and the train may be pulling into the station. Could get...interesting...
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04/07/19 "And then I 'punished' you by making you lick my pussy after I let my other 'boy' fuck me." --Mrs. Twisted
belocked
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Re: Dating and chastity advice

Post by belocked »

Our schedules mean we don't get to see each other until next next weekend. My mind was racing yesterday and I decided to put on my jailbird. I mentioned it in passing when we were chatting in the evening but she didn't react. This morning she asked if it was still on (it is) so I know that she's interested. I have the keys so we both know I can remove it at any time. That's good for both of us now but I'm already thinking ahead to when (not if) she decides to keep the key. We're far enough apart that I'll need an emergency key that I can get access to.

I know I've opened Pandora's box and it's definitely going to get ...interesting...

I should restart my journal.
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bondinchas
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Re: Dating and chastity advice

Post by bondinchas »

belocked wrote: Thu Apr 08, 2021 12:30 pm ... it ended with the comment "I want to see it on you tomorrow".
I didn't need a 2nd invitation so the next day I put it on when I got up early. She discovered it when I went went back to bed and gave it another close inspection. It stayed on for a few hours and there was some fairly intense teasing. She'd said I would have to wear it until I left that afternoon but changed her mind and let me out, but she did say that she would expect me to be wearing it when I arrive next time. Now I'm just wondering how far ahead I should prepare myself. ...
How far ahead? why not start now? Why don't you wear it all the time when she's not there?
Now that you know that she's not adverse to it, you might as well get the full benefit, and she will too if you're already denied and waiting for her to decide when you will be unlocked. Choose the moment when you tell her how long you've been wearing it "for her". She obviously enjoys the tease side of it, does she understand the benefits that she will get as well?
"Go for it!"
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belocked
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Re: Dating and chastity advice

Post by belocked »

I've posted in my journal so you can follow the latest developments.
bondinchas wrote: Sat Apr 17, 2021 9:22 am Why don't you wear it all the time when she's not there?
I know from experience that I need to build up to longer durations. I had to stop early last time, and I have a medical appointment this week, but I'm ready for a week plus for the next lockup.
bondinchas wrote: Sat Apr 17, 2021 9:22 am She obviously enjoys the tease side of it, does she understand the benefits that she will get as well?
She's a very quick learner :o
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