Unsure and possibly unwilling Keyholder here
Hi there! I wasn't really sure what to title this post, but I'm hoping you guys can provide some help!
So I have a "friend with benefits" that I've known for about 4 years. I haven't actually been physical with him since June of 2019, nor even seen him at all since then (he lives an hour from me). We have a long sordid history which is too long to get into here, but one of the big overarching themes to our relationship is a lot of push and pull. He'll date someone else but then while he's dating her he'll still reach out to me, tell me he wants my strap in his ass, can't stop thinking about fucking me, etc. I never indulged him while he was in other relationships but I will admit I played along with it over text. Plus I was living my own life and dating other people as well. We went long periods of time without even texting, but started texting regularly again in November.
We are both completely single now and have been talking about getting together again, and have planned multiple dates to meet, but then I got COVID, then the holidays, yadda yadda. I know there is some reluctance on my end to get together with him merely just to fuck. The idea of him coming over here and just fucking again doesn't really fit into my plans right now... I want more (not even necessarily from him, just from the person I'm fucking).
Well the other day we were on the phone and he told me he had a surprise for me. He asked if we could FaceTime and when we did, he panned down and showed me he was wearing a chastity cage! Now, we had discussed this in the past in terms of it being something he was interested in, and sharing porn with that theme, but it had never gone beyond that.
I have to admit the sight of him in the cage was extremely hot, and I told him I couldn't wait to see him again. The thing is, once we got off the phone... he texted me told me he was giving me the key. And he told me that he always should've been at my side, and now this way I'll be able to make sure he can't stray again.
I was a little taken aback by all of this. It seemed like a big revelation to me.
He wanted to know if I was happy and turned on that I would have the key. Of course my initial instinct was to say yes, the sight of it and the fact he bought a cock cage and put it on was extremely titillating, but I was not sure of what being the keyholder meant to him. He replied, "It means you own my cock." Well, I get that part, but I feel there's an emotional component here that I'm not getting. I told him we needed to talk in person about this, that this was not a text conversation. He wanted to drive to my place that night to give me the key, but I had plans. So he's coming over later this week.
So... I realize this is a huge responsibility. Do I want it? Can I handle it? I feel as though I'm being thrust into this position and I'm not even sure if I want it. If he plans on being locked until I let him out... that means I have to see him more often. I mean how long can he realistically be in the cage without me letting him out? I don't know yet what his expectations are (of me? of us?). I really need help disseminating this.
Can you be a keyholder for a man with whom you're not in a relationship? I understand there are purely transactional relationships where a domme will hold a key for her sub, but obviously this is not one of those situations.
Any advice? So glad to have found this board!
Wow that is a lot for him to hit you with over facetime. From a transactional standpoint of just doing this as friends and having fun it would certainly be interesting.
My concern would be it sounds like he wants to be a lot more than friends when he says things like "he always should've been at my side, and now this way I'll be able to make sure he can't stray again" --- that is NOT a Friend With Benefits situation.
I think before you take the key you need to let him know how you feel and that you are not ready for a steady commitment and to ALWAYS be by his side but that you are still thinking of this as fun and a friend based thing rather than an exclusive and series arrangement. Since you still like him as a friend and are not sure where this is going i would say don't be too harsh --- just because you are not ready for that now doesn't mean you won't ever be.
Once he recognizes that you won't be there to see him and tease him every day and he is still your friend not your everyday live in boy friend so he better get used to not cumming too often since you are not going to start seeing him every day then you can discuss if you should really be his key holder. Set some boundaries and stick to them - he can't just show up and he can't expect you to be there 3 or 4 times a week for example.