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At what point do you know it's time to let loved ones and family know about the femine side you have been exploring and developing for many years with out them knowing about it?
What are good, bad and plain ugly truths about letting them know about your private little world?
There is no easy answer since it depends on so many factors. The first is do you want/need to anounce this? If you intend to live openly en femme, then obviously people will need to know. If you prefer to keep it private, few people need to know. If you are inbetween, then you need to pick and choose who knows. I am on a "need to know" basis. Since I dress around the house, I feel my wife needs to know, and does. My adult children live along way away so do not need to onow, so they don't. I would have no issue with them knowing. And feel completely confident in their acceptence, but there is no need. If you have a close relationship with family members who are around a lot, and who affect your dressing, then telling them has more purpose and gives you more freedom.
For me, I reached a point where keeping my feminine side secret was starting to quietly damage the relationship I had with my wife. I hated hiding it from her - it felt dishonest, and that weighed on me more than I expected.
When I first opened up, I only mentioned the idea of wearing panties and stockings during intimacy. She was shocked, understandably, as I’d always presented as quite a typically masculine guy. But she was so sweet about it - she even went and bought me a pair of black lace panties not long after.
From there, we began slowly introducing more of that side of me. Over time, I hinted that I’d love to try wearing clothes, heels, and expressing that deeper feminine energy. Again, there was surprise (and I think some worry I might be gay), but as I reassured her - and continued showing her I was still me, just with a little more softness - she gradually relaxed into it.
These days, she occasionally encourages Jenny time, and I think she’s come to enjoy the sensual, tender side of me that comes out through it. I know I’m incredibly lucky to have a supportive partner, and I never take that for granted.
That said, I’d be lying if I didn’t admit there are still darker days - moments where I regret telling her, where I worry she sees me differently or thinks less of me for it. Sometimes I long for the simplicity of being seen as just the masculine version of myself again. But I’m learning to weather those storms, knowing this is all part of becoming more whole and honest with myself - and with her.
This a difficult thing in any circumstance. I wrote two articles on 'Who to tell' I am not sure how to link them but they will be under my profile.
I am not in a marriage but there are other considerations, you know your wife, her thoughts, attitudes and view on life so then you could know how she feels about Trans and crossdressing. Even though she may be accepting, if it were another family member or friend could show a level of acceptance. Is there anyone you both know that is an out Trans or dresser? You could test the water and drop it into appropriate conversations as a cast aside comment not to dwell on.
However when it is your partner the reaction can be very different, no one can say how it will go as some will accept without question to all sorts of levels of acceptance to the absolute horror of revulsion and what may go with it which is a divorce, as harsh as it may seem but that's the truth.
If you feel you must come out to her consider if she may actually know, any dressing in the past for a fun event. finding an item you have left out or any covert comments.
I think we all agree it is a difficult thing to do and there is no real script to follow as you have to do it yourself. Already you have been given some sound advice and am sure there will be more to help you should you need it.
I would say take your time and do your homework and if you do go ahead you know we are here for you.
I told my wife when I reached the point of being tired of the hiding, sneaking and lying. I was prepared for any eventuality, even divorce. I needed the release of telling her so that I could remain sane.
As for the rest of the family, they still don't know and we keep it that way to keep the peace. From their attitudes we know it would not go well and we wish to see the young ones grow and be part of their lives. Maybe someday they will find out. Same is true for friends.
I told my other half and immediate family last year, when I first realised that I was now doing more than just 'playing girl'. I was soon living full-time, and I've been out to the whole world since about two months in 🙂