Broaching the subject of masking with a partner

 So I've been alluding to this for probably years now, that I'll broach the subject of masking with my partner and perhaps make some content to share. 

I keep finding myself chickening out when brining up the subject of masking with my partner. In the past, shared my masking fetish with a friend that became a semi-brief and semi-complicated romantic relationship. I had a few sexual masking sessions with this person I'll refer to as R. 
R was/is trans, very open to gender play, very open to using prosthetics, etc. I shared pictures of masking with them and they were always very supportive, but when it came to actually playing with them (or having sex) while masked, I could feel that things would suddenly become awkward. 

At this point, R and I had become very close as friends and had also crossed the threshold of being sexual partners (this was years ago). They were a good sport with masking, however it felt more like they tolerated it, rather than enjoyed it. While masked, I started feeling more silly than sexual and from these exchanges, I ended up recognizing that masking was something I would only be doing in private (by myself). Since it felt especially uncomfortable to be so vulnerable with someone to be received in a way where it was clear that they were 'trying their best' to go along with things. 

I was hoping that sharing masking and playing with R would have been an experience that would build up my confidence with masking with others. However, it did quite the opposite. R was never derisive or judgmental of me outwardly, but after our few masking sessions, it felt like our connection became strained and awkward. For various other reasons, we dropped out of touch, but the impression from the experience remained. 

With my current partner, we've had some sexual exchanges where I've been masked, but only while she's been blindfolded. It's only after the fact that I'd let her know I was wearing a mask, to which she seemed to have no response or concern about. I've also told her that I was wearing a mask and she was wearing a head-covering since we were making these videos, therefore it encouraged anonymity. However, I haven't directly stated that masking is an interest of mine and it's getting to a point where I'm very much wanting to make some videos with her while she is wearing a female mask. 

For our videos so far, I feel like I haven't been very up front in basically saying afterwards, "oh yea, I was wearing a mask," but never really stating my interest in masking. I think that if I simply pull out a silicone mask for her to wear and say, "put it on, it'll make you anonymous for a video," it may not be received well. I worry that without proper context that she will take it as me saying/thinking that she is ugly or that I want to sleep with someone else (hence put on a different face). So I don't want to offend her in any way, but it feels like in order to avoid this, I'll need to open up and be vulnerable again. Given my experience with R, I'm somewhat worried about this. 

So I'm curious if others have had experience with introducing masking to their romantic partners? If you have, how did you do it and how did it go? Does your partner participate in masking with you? What are some of the great things and not so great things that go along with it? 

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The plan I have now basically falls into a few categories:
1) present the mask and say that it's for one of our videos and that it would be useful to make her anonymous for the xxx clip. 

2) present her mask and my mask (mine is male) and approach it like a fun 'role play' scenario. Probably having an initial show and tell session with her, then later do a full dress-up session + a video (if all goes well). 

3) Sit her down and discuss my interest in masking and history with masks, then gauge interest from there. (this is the option I think is best, but also feel like I'll chicken out and not go through with the conversation). 

I think the hardest obstacle that I face with my partner is that our schedules don't sync up very well. Most of the time we only see each other right when we wake up and are getting ready for work or around 10pm-12am where she's coming home and feverishly eating a very late dinner, then promptly going to sleep. Much of the time at night when she gets home, I'm typically already in bed. 

The ideal share scenario I've been waiting for and hoping for is one where it's not the middle of the night, we're about to become intimate, then I initiate one of these conversations. The few times this has happened, we've typically worn latex and had sex or I wear something and have sex. It's been a very few and far between occasion and when these opportunities arise I think, "ok, we have this conversation and it totally ruins the mood and I miss the chance to have some fetishy sex OR we have some fetishy sex," and in the past I have always chosen the latter. As of now, my basic plan is to wait for this next opportunity and go with one of the options above, based on how the situation feels. But I did want to get a sense of whether anyone reading has had similar experiences and had any tips or suggestions to share? I'm also just open to suggestions in general, so thank you all in advance who comment. Thanks!