Dating and chastity advice

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belocked
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Dating and chastity advice

Post by belocked »

As I've just posted in my journey, I'm coming out of a divorce and wanting to re-engage with the world. Part of that is dating. I haven't dated in more than two decades so the whole social media part of it is new to me but I can already see the benefits for finding people who might be interested/interesting. I'm just starting to dive in and hope to make progress very soon. I just hope there won't be another full lockdown of bars and restaurants as COVID is getting worse here quickly. How could anyone start dating with no social venues?

In the back of my mind is the chastity thing. When, if ever, should I bring it up? I'd be really grateful to hear any *real* stories from people who have been through it. Serious advice is also welcome, which is why I've come here not to many other forums where I'd be advised to lay it out immediately and ask someone to become my dominating goddess. To me chastity is a possible way of cementing a fun relationship and nothing more.
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Steve2059
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Re: Dating and chastity advice

Post by Steve2059 »

Have you thought of using a kink dating site such as Fetlife?

There's a lot of debate as to whether chastity is a popular or a rare kink (for obvious reasons we tend not to advertise) but my guess is that it's a bit left-field as opposed to lingerie or a bit of light bdsm, and most of the cages that get sold end up in drawers (I have a collection myself but can only use one at a time). With a site such as Fetlife, if chastity is a must-have in a new relationship, you can be honest from the start.
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Tom Allen
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Re: Dating and chastity advice

Post by Tom Allen »

Here's my advice, worth what you paid for it.

If you are dating outside of your social circle (ie, she's not known to your friends) by the 3rd, 4th, maybe 5th date, you need to let her know that you're a bit kinky. Don't make a big deal over it, just explain that just as kids, pets, job, religion, politics, etc., are potential compatibility issues, so is (are) this little kink that you have.

A few dates in, and women won't feel like they've invested too much time. They'll either try it or not. If they aren't into it, then everybody moves on, and no hard feelings.

By the same token, without having invested 20 years of marriage, it should be easy for you to raise the subject without feeling like you're going to screw things up.
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Critter228
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Re: Dating and chastity advice

Post by Critter228 »

I agree you should bring it up kinda quickly. Not right away. Not in the first three or more dates. But once my gf started spending the night regularly I told her. It was awkward but she accepted it. She didn’t do much with it but she knew it. I’d bring it up occasionally, but not in a weird way and she has been okay with it. Sometimes embracing it.

I didn’t tell any of my other gfs about it. I should have. Maybe they wouldn’t have accepted it. Or maybe it would have been amazing. In hindsight I believe my ex was a borderline Domme. She liked making decisions for me and enjoyed denying my orgasms on occasion, wanted to do things with my butt and enjoyed the one ruined orgasm she gave me. But she’d never talked about it and without it being in a kink context I found these to be negatives. I thought she was just being selfish and weird. Looking back I may have missed an opportunity to have a gorgeous Asian mistress. But I don’t think she’d even admitted it to herself that’s what she wanted. So we never clicked.

Anyway, I rambled. But best to get it out of the way semi early. Don’t wait until you’re married with three kids and say “can you put this cage on me?”
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belocked
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Re: Dating and chastity advice

Post by belocked »

Thanks for the advice so far. I can see that it make sense to bring it up fairly early in a relationship to make sure it's not a show-stopper for her, together with the other mild kinks. Critter228, it's nice to know that someone has been there already and survived.

Steve2059, Fetlife sounds an interesting idea, but it would seem to mean defining myself by my kink(s). I'd prefer to find someone who likes me and puts up with kink(s) rather than someone who likes kink(s) and puts up with me. But thanks for the thought.
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Critter228
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Re: Dating and chastity advice

Post by Critter228 »

I just told her it was something I was into and i could stop if she didn’t want me doing it or if she was disgusted or alarmed by it. She’d never heard of it and doesn’t fully understand it (heck neither do I) but she supports it now and understands it’s a part of who I am, it doesn’t define me and it’s not an addiction, tho the rush feels like it sometimes. Just another part of who I am.
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Re: Dating and chastity advice

Post by TwistedMister »

belocked wrote: Mon Sep 28, 2020 11:38 am Thanks for the advice so far. I can see that it make sense to bring it up fairly early in a relationship to make sure it's not a show-stopper for her, together with the other mild kinks. Critter228, it's nice to know that someone has been there already and survived.

Steve2059, Fetlife sounds an interesting idea, but it would seem to mean defining myself by my kink(s). I'd prefer to find someone who likes me and puts up with kink(s) rather than someone who likes kink(s) and puts up with me. But thanks for the thought.
I don't think that it would necessarily be 'defining', but it would certainly increase the chances of arriving at a commonality without conflict. If you are fishing for salmon, you aren't going to do it in a trout pond.

If it's on your mind to this extent, then it is obviously something that has some level of importance for you. Why not improve your odds of finding someone compatible? You're still going to go through the same process of meeting people, and advancing a relationship based on many other criteria. Why would either you or anyone else tolerate each other based merely on kink?

It wouldn't have to be your sole 'hunting grounds', you could still pursue other avenues of meeting people.
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Re: Dating and chastity advice

Post by locked4her55 »

Critter228 wrote: Mon Sep 28, 2020 10:20 am Don’t wait until you’re married with three kids and say “can you put this cage on me?”
:lol:
Maybe after three kids she would be the one suggesting the cage. ;)
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Re: Dating and chastity advice

Post by Clearstatic »

My biggest regret is not being confident enough to be who I am. After my divorce to my first wife at 25, I had a whirlwind of partners and dates. My current wife and I ended up pregnant and stayed together, we had met before my first marriage and we had/have a strong connection. But I was ashamed of my kinky side and not getting it out there from the start really set things back.

Maybe we would still be together maybe we wouldnt. But it would have been much more fair to her to have that knowledge before she committed herself to me.
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belocked
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Re: Dating and chastity advice

Post by belocked »

I'm recently divorced and have found a new girlfriend. This last weekend was the 4th time I've stayed at her place and i decided to take the plunge. I'd mentioned bondage once before to a reaction "I'm not into it, but I'd be willing to try". So this weekend I brought it up again and she was much more interested to try it; first she wanted to try it on herself, then on me. She enjoyed both, and later that day I decided to tell her more. She was puzzled by my description of a cage and wanted to see it immediately so I got my Jailbird out of my bag. She inspected it carefully while saying it seemed very heavy and looked very uncomfortable. She was amazed that I'd worn it once for a month. That conversation didn't last too long, but 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.

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.

So the advice here was good. If you can have an open and honest conversation with the right person there's no need to wait a long time to introduce chastity.
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