Dating Advice with a Focus on Chastity

As I mentioned in my recent update, I’m emerging from a divorce and eager to get back out there. Dating is part of that mix. It’s been over twenty years since I last dated, so social media feels like new territory for me, though the perks of finding potential matches are already clear. I’m just beginning to explore this world and expect things to move forward shortly. My only worry is another full lockdown in bars and restaurants as COVID cases spike here again. How can anyone date without places to go?

Also, there’s a question about chastity lingering in the background: when should I bring it up? Any real experiences from others who’ve lived through this would be greatly appreciated. Genuine advice is welcome too; that’s why I’m here rather than on other forums where people might say you need to declare everything immediately and beg someone to become your dominant goddess. To me, chastity is just a way to add fun structure to a relationship, nothing more.

Have you considered using a kink-focused dating platform like Fetlife? There's ongoing discussion about whether chastity is common or rare (for obvious reasons we don't always advertise it heavily), but I suspect it sits slightly outside the mainstream compared to lingerie or light BDSM. Many cages end up in drawers because they aren't used daily—I have a collection myself and can only wear one at a time. On Fetlife, if you need chastity as a core requirement for a new relationship, you can be upfront about it from day one.

Here is my suggestion, worth exactly what I'm asking for. If you are dating someone outside your usual circle (so she isn't already known to your friends), by the 3rd, maybe even the 4th or 5th date, let her know you have a kinky side. Don't make it a huge issue; just explain that like kids, pets, career, religion, or politics, this little quirk is another compatibility factor. After a few dates in, women won't feel they've wasted too much time if things don't work out. They will either give it a try or pass. If she isn't into it, you both move on with no hard feelings. Similarly, without the weight of 20 years of marriage behind you, raising the subject should be easy and won't feel like risking everything.

I agree that bringing it up fairly quickly is wise. Not immediately upon meeting, but not waiting until the third date or later either. Once my girlfriend started sleeping over regularly, I told her. It was a bit awkward at first, but she accepted it. She didn't do much with it practically, but she knew about it. I mentioned it occasionally without being weird, and she has been fine with it, sometimes even embracing the idea. I didn't tell my other girlfriends about mine back then; perhaps I should have. Maybe they would have accepted it, or maybe it would have worked out beautifully. Looking back, I think my ex was a borderline Domme. She liked making decisions for me and enjoyed denying my orgasms sometimes, had an interest in anal play, and appreciated the ruined orgasm she gave me once. But since we weren't really in a kink context, I viewed these traits as negatives—I thought she was just being selfish or odd. In retrospect, I might have missed out on having a stunning Asian mistress. However, I don't think she had even realized what she wanted herself, so our connection never quite clicked. Anyway, that's my story. Best to get it off your chest semi-early rather than waiting until you are married with three children and asking, “can you put this cage on me?”

Thanks for the feedback. It makes sense to introduce it early enough in a relationship so it isn't a dealbreaker, especially alongside other milder kinks. Critter228, good to know someone else has navigated this before and survived. Steve2059, Fetlife seems like an intriguing option, but it feels like it might mean defining me by my kink(s). I would rather find someone who likes *me* and tolerates the kinks, rather than someone who loves the kinks and tolerates *me*. But thank you for the suggestion.

I simply told her it was something I enjoyed and that I could stop if she didn't want me doing it or if she felt disgust or alarm. She had never heard of it before and doesn't fully understand the mechanics (honestly, neither do I), but now she supports it. She sees it as part of who I am; it defines me less than being an addiction, though sometimes the rush feels that way. It is just another piece of my identity.

> 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 Fetlife necessarily means 'defining', but it certainly boosts your chances of finding common ground without conflict. If you are fishing for salmon, you won't cast your line in a trout pond. If this matters to you enough that you are thinking about it, then clearly it holds some importance. Why not improve your odds of finding compatibility? You will still go through the normal process of meeting people and building relationships based on many other criteria. There is no reason either party should stay together solely because of kink. It doesn't have to be your only 'hunting ground'; you can still explore other ways of meeting people.

> 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: Perhaps after having three children, she might be the one to suggest putting it back on.;)

My biggest regret is not being confident enough in my true self. After divorcing my first wife at age 25, I had a whirlwind of dates and partners. My current wife and I became pregnant and stayed together; we had actually met before my first marriage and share a strong connection. However, I was ashamed of my kinky side, and not presenting it from the start really set us back. Maybe we would still be together now, or maybe we wouldn't have been. But it felt much fairer to her that she knew about this part of me before committing.

I am recently divorced and have found a new girlfriend. This past weekend marked the fourth time I stayed at her place, so I decided to take the plunge. Before, when I mentioned bondage once before she had said, "I'm not really into it, but I'd be willing to try." So this weekend I brought it up again, and she seemed much more eager to give it a go; first she wanted to experience wearing one herself, then having me wear it. She enjoyed both experiences, and later that day I decided to explain more about my practice. She was puzzled by my description of the cage but asked to see it right away, so I took out my Jailbird from my bag. She inspected it carefully, noting that it seemed heavy and very uncomfortable-looking. She was amazed that I had worn one for a full month once. That conversation didn't last long, but she concluded with, "I want to see it on you tomorrow." She gave me the green light without needing further prompting, so the next day I put it on early in the morning. She noticed when I went back to bed and examined it closely again. It stayed on for a few hours, accompanied by some fairly intense teasing. Although she initially said I would have to wear it until I left that afternoon, she changed her mind and let me remove it earlier; however, she did state that she expects me to be wearing it when I arrive next time. Now I am just wondering how far ahead I should prepare myself. I should add that she is quite confident, so I thought she would take an interest. Maybe this will simply become a game between us, or maybe it will grow into something more than I am ready for right now—but I am open to anything at this point. I have a dermatologist appointment later in the month, so I know I will be out and about then, and she isn't (yet) ready to take permanent possession of the keys, so control remains with me for now. But seeing the look in her eyes tells me she might truly step into charge. So the advice here has been good. If you can have an open and honest conversation with the right person, there is no need to delay introducing chastity.

This thread could really use the wisdom of our Keyholder members. Their perspective would be helpful and enlightening. What do you say, Keyholders?

> 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 are on the right track, and the train might just be pulling into the station. It could get...interesting...

Our schedules mean we don't see each other until next weekend. My mind was racing yesterday, so I decided to put on my jailbird. I mentioned it casually while chatting in the evening, but she didn't react visibly. This morning she asked if it was still there (it is), which confirms her interest. Since I hold the keys, we both know I can remove it whenever I choose. That works well for us right now, though I am already thinking ahead to when (not *if*) she decides to keep the key herself. We live far enough apart that I will need an emergency key accessible to me. I feel like I have opened Pandora's box and things are definitely going to get ...interesting... It might be time for me to restart my journal.

> 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 whenever she is away? Now that you know she isn't opposed to the idea, you might as well get the full benefit from it—and so will she if you are already denied and waiting for her to decide when you unlock. Choose a moment to tell her how long you have been wearing it "for her." She obviously enjoys the teasing aspect; does she also understand the benefits that come with being in charge? "Go for it!"