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Tell your partner about crossdressing

Talking about crossdressing
Experienced Mistress Olivia

Listen to me read you this crossdressing audio.

Have you told your partner that you like to wear women’s lingerie?  Or, do you keep quiet about your love of the silky panties?  For some of you, your crossdressing only comes out to play when you are on travel.  Others of you have a stash of items that you might collect, wear and then purge again and again.

When to tell and why

I’m often asked how to tell a partner about a fetish or secret desire.  For the girly girls, I think it often comes down to this:  is your dressing a sometimes fun kink OR is it an expression of gender identity?  The answer to that question makes all the difference in terms of whether to tell your partner.  There are LOTS of considerations but that’s the beginning of the conversation.

Here’s what one crossdresser says:

“Oh my, this is such a tricky subject to get right! I told my beautiful GF a few months into our relationship because I couldn’t bear the idea of having that kind of secret between us. It was terrifying! She has accepted my femme side but admits she doesn’t really understand it (that’s OK, I don’t either!). She doesn’t really want to be part of it, but knows that it’s something that I do. I can’t really ask for more than acceptance…”

Who know all your secret desires?

Secret desires are often about sex but I know that a lot of you want to confide in more than just erotic topics.  Who do you tell?  Who knows you for ALL of you?  That’s something else to think about.

Your Experienced Mistress,

Ms Olivia


12 comments to Tell your partner about crossdressing

  • Sara

    I think a lot of it comes down to trust. For me, in my relationship at that time, it was more important to be open and honest and to do it early on. I realise this may not be the same for everyone! It helped a lot in the openness that we continue to share, because I’d never made myself so completely vulnerable before. The bonus (and it is a bonus!) is that we’ve been able to share more in our sex life. Win, win! I guess it’s harder if it’s a secret that you’ve kept from your significant other for longer. There’s no ‘right’ answer, only the one that feels right to you. It’s never NOT scary though 🙂

    • Olivia

      Thank you for your followup comment Sara. The desire to be fully seen and known is huge for ANY person, not just someone with anything outside of the supposed “norm” in terms of sex. It takes great courage to be vulnerable to another person. YOU have courage. You make my heart smile.

  • yvonne

    Hi Ms

    I just had a visit from my brother and even though we had a good visit it was very stressful for me. I could not even keep up with my most basic feminine pleasures witch for me means a night gown and wig and perfume and a bit of jewelry. It continually crossed my mind just to tell him I need to do this but I know it would bother him and make him uncomfortable. He knows about my dressing we just don’t talk about it.


    • Olivia

      Ahhhhh, that’s the most icky thing ever … I’m so sorry yvonne, so very very sorry!

    • yvonne

      Just one of the things I deal with. I know I am not alone or exclusive in this. I will guarantee there are many who have it much harder than I do and my heart really goes out to them.


      • Olivia

        My heart goes out to anyone who has to “cover up” who they are. I know that feeling in various situations and it’s icky. Now, that doesn’t mean everyone get to (or should) know everything. I’m a firm believer in privacy. There is a middle ground between “everyone” knowing and being isolated and feeling ‘not known.” I’m sure not showy about my love of kink in all situations … and that’s the way way it should be … I’m grateful that I do have people who do know that side of me. I do feel “known.” I wish every femme girl that same feeling of being known and adored. I also wish an unlimited clothing budget and world peace. hahahahahaha

  • Being TS myself on HRT decades now. It’s like I’ve lived full time in girl world some 13+ years already and occasionally having to slide in between at times now. Even in this day and age when being TS is way more exceptable than it once was, when I first transitioned. Even my family from my parents to even my sister thinks I should just go back to being full time as did they say I was more content or happier just being me. Which is a huge step, even for them, because they disowned me years back for doing just that.

    What I’ve learned over the years is that you can’t force transexualism down progress throats, but rather they have to want to Maybe understand more, in order for it to work or have feelings for one. Same as it word be for cross dresses I’m guessing.

    I’ve been cleared by two separate medical boards and two surgeons as well as good to go on SRS surgery. N yet this post girlfriend, which I told her off myself long before it became steady between us, as I didn’t want to lead her on. So we were platonic friends, which I enjoyed. Maybe it was my fault to tell her I wanted to share a cock with her. Lol. Probably not a good thing. Probably want smart of me to tell her I loved clothes that made me look good in cocks eyes. As earlier she had told me I knew more about fashion, than she did. Haha.

    Oh well. I still felt horrible, as now I’m friendless once again other than online friends, which I still value very much.

    Thank-You for the blog, as do I love it so

    • Olivia

      ahhhhhh, I’m so sorry and I get it. It’s hard to connect with someone even without adding anything “outside” into the mix. I have a friend who loves fly fishing and he laments finding a woman who is equally passionate about his hobby (and who is still unattached to a fly fisherman)….so it’s not just with dressing en femme or gender reassignment. I am constantly surprised at how hard it is for human beings to just “let others be” … and yet, on the flip side, if dressing en femme isn’t something that the other person wants to experience then, like you can’t, it can’t be forced. Sigh. Isn’t this the ultimate conundrum?

  • Petey cream puff

    I did it Ms Olivia-I did fashion show with my masseuse yesterday and tried on 10 dresses!! It was dream come true Ashe Saudi looked so cute and adorable in them! She wants to barrow one of my dresses for her sons wedding in August which she invited me to. Last week she was thinking about me in dress and said she wants me to wear when we go shopping later this year when I buy lipsticks/perfumes/lotions along with me getting makeover. I’m her cream puff girlie boy forever now as she has me wrapped around her fingers and nails dug into me with no intention of ever letting me go.

  • Emily

    Hi Olivia, i don’t​ have a partner to possibly tell this to but I do have a close friend who has done so much for me, been there for me when I was hurting, so I feel awful about not letting her know this about me. I mean it is such a big part of me, so it’s a little unfair that I don’t share. The problem is, I don’t know exactly what “It” is.

    (((( WOW and WOW Emily has more to say and I think this is such an important and thoughtful comment and topic I’m turning it into a blog post)))))

    • Olivia

      WOW !!!!!!!!!!!!!!! You have some amazing comments …. I’m turning this one into a blog post as well because I know for a fact that you are expressing something many people experience! THANK YOU sweetie, thank you!

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