I'm lucky enough that my wife is ok about it when I wear lingerie. I don't want to jeopardize this, but have developed a curiosity about taking things further. I'd like to try wearing a dress, heels, makeup, etc., and would love her to give me a makeover. Any advice on how to take things forward would be appreciated. It feels difficult because during our conversations when I opened up about wanting to wear lingerie, I reassured her that I didn't feel the need to dress up as a woman.
There are a million ways to come out to someone and almost all of them are wrong, lol.
I know that's not helpful at all, so let's talk about what I feel is the best way to have The Talk.
Be honest.
Be gentle.
That's it.
Again, not helpful.
You know your wife better than anyone on the planet (I assume) so you probably know how to have big, relationship-changing conversations with her. I wouldn't be surprised in your time together if you've already had uncomfortable and difficult conversations about finances, careers, family, and other big things. You probably know how to talk to her about these things. Some people need big conversations in a very direct way, others need to be eased into them. Timing is important, too. If my wife and I need to have a big talk about something, we don't have these conversations right before one of us (or both of us) are getting ready to go to bed. We've learned that after dinner while we are both sitting at the table is a good time for serious chats. Have The Talk at a time that works. If she had a terrible day at work it might not be a good idea to chat about makeovers as soon as she gets home.
You can acknowledge that your feelings have changed. She may feel you were not being honest (which is valid) when you originally came out about how far you wanted to take things so be prepared for that. Be prepared for other questions, such as whether or not this is leading to transitioning or asking about your gender identity. Lingerie is one thing, makeup and skirts are another.
You more than likely recall how the initial conversation about lingerie went, so you have a little precedence about how she MAY react. This aspect of ourselves is a lot to ask of our partners, and many of our partners feel alone and overwhelmed in all of this. She may feel that she has no one to talk to about this. Afterall, there's a lot of stigma about "men who wear girl clothes" and she may be reluctant to open up to her friends about her feelings about this.
If you are going to take your dressing in a new direction then I don't think trying high heels or anything else behind her back is a good idea. She may be hurt or angry (and justifiably so) that you are not/were being honest with her (or with yourself).
Relationships with people like ourselves are not easy and there's a lot to consider. I've written on this topic before and I would encourage you to take some time reading my thoughts to similar questions.
Love, Hannah
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4 comments
I’d love to get a makeover. Nobody knows about my secret crossdressing habit so it’s difficult to know how I’d ever find a way to get someone to do it. My ultimate dream is for someone to ‘force’ me to have a makeover. I’d be made to change into lingerie, a dress and heels before being tied to a chair while they put make-up on me. A wig would then be fitted before I was made to spend time as a girl. I’d be blackmailed to keep doing this by the threat of exposure using photos taken of me having the makeover and while being all dressed up. One day, maybe?!
Hi Alana,
I have purchased lovely shoes 👠 hear at xdress. Also Pleaser shoes are my next favorite store for all types of shoes.
Just be honest. She accepts the lingerie and will likely accept you dressing up.
Other than SD which really don’t have me comfortable in. You have mentioned another supplier for men’s feminine footwear. Please tell me where. Alana