Getting Your Parents On Board!

Hello loyal readers! I would like to take this moment to personally wish you all the best, and hope you're coping under this ongoing COVID mess. It has been a while since a more personal blog has been posted, so today let us take the time to discuss how to approach crossdressing with your parents / in laws. 

Last October, I had summoned the courage to present myself en femme around my girlfriends parents. I made this decision because I am in a very serious relationship with this woman, and her parents deserved to know who I really am. After all, this seemed preferable compared to them finding out beyond my control. When I visited, I wore a very androgynous outfit as to not completely shock them. A long black tunic top, black leggings, and basic foundation with eyeliner was the look I choose. Initially, all went well and I actually felt quite comfortable while there. 

My girlfriends mom said I looked cute, and her dad seemed fairly indifferent to it. When I left their house that day I felt quite proud, as I had overcome one of my biggest fears. After all, I had been putting off visiting them for several months as I felt it would cause upset among them. Unfortunately, despite my good feelings while there, I was right. Not even a few hours after getting home, my girlfriend received a text from her parents. In it, her mom wrote that I was not right for her, and that she should leave me immediately. 

Even though my girlfriend proclaimed her undying love for me to her parents, it had no effect. Every time she visited them following this event, they both tried to create a rift between us by bringing up things my girlfriend had been previously insecure about. This included them stating I was gay, that I would inevitably get a sex change at some point, and that I was not welcome in their home. This went on for several months, however it reached its peak earlier this month when both her mom and dad stated I was a freak, and that I was the lowest of the low. Since my girlfriend and I are incredibly happy together, this caused her to make the unfortunate decision to cut her parents out of her life, at least for now. 
This example is probably all of our worst fear; to be called a freak and judged so harshly just because of how we present ourselves. By contrast, both of my parents were accepting of me, despite some initial shock to it since they had no idea about this side of me at the time. So what is the lesson here? I personally feel I did the right thing by confronting my girlfriends parents by choice, considering the fact that I dress en femme every day. I do not even possess any male clothes anymore, aside from my gym clothes. There is no way I could have repressed this side of myself for decades to come, without her parents finding out eventually. Besides, I spent the first 20 years of my life repressing who I truly was. 

So after its all said and done, I think how one chooses to confront their parents or their SO's parents is entirely up to them. If you're like me, and crossdressing is a part of your everyday life, you will inevitably have to have that confrontation. However, if you only underdress or crossdress in your private time, then perhaps keeping it hidden from people beyond your SO is best. However, the main thing I would like to say to you all is; no matter how your parents / in laws may react, there is absolutely nothing wrong with crossdressing. We all possess our own beliefs and convictions, and how other people react is not our fault. As long as you are happy in what you do, that is all that matters. 
I could easily go on about this topic, as it is a very personal and emotional one. I truly empathize with those who have been in the same position. So let us take the time to vent. Have you confronted your parents or in laws about your crossdressing? What happened? What did you learn from it? We are all in this life together, and support is absolutely critical. 



I came across your blog as I was checking out the XDRESS website. I am an older single male and have enjoyed wearing lingerie for decades. I don’t know if that is considered cross-dressing as I only do so in the privacy of my own home. I have told a few women that I was in a relationship with (no longer) that I wore lingerie (mostly panties and sheer gowns) but they haven’t seen me in them. I have thought about telling my grown adult children as I’m tired of hiding this part of my life. It (wearing) is important to me as it gives me great pleasure to wear as I’ve known for a very long time that I have a sensual soft side of me that needs to be expressed and do so by wearing what gives me great comfort. As mentioned I’m single and would love to share this important part of my life with the right person but so far this has alluded me.

Life is short and after coming this far in it its become important to me to be who I am and not be ashamed of it.

John September 26, 2021

Thank you for this touching personal post. I wish I had answers for you in this situation, but I unfortunately don’t. I can share some of my own experience though.

I’m in a pretty complex situation. I’m a trans man /and/ I enjoy crossdressing, so I’ve had to balance sort of a double coming out. We had to deal with my SO’s parents not seeing me as a man due simply to my body shape (I was pre surgery when we met) and then also with the fact that I do occasionally wear women’s clothing on top of that. Even though the rest of the world sees me as a man now, at least when dressed in men’s clothing, I think the combination of the two things may have made it so that the SO’s mother will never see me as such. His father has come around to it though.

I’m hoping it will just be a process that takes time, but if it doesn’t, I know that my SO loves and supports me in both my transition and my occasional crossdressing, and that’s what really matters.

Joshua March 11, 2021

Well at the moment I am living with my girlfriend in her parents house. My nails are always painted in pink, sometimes I use eyes lashes and leggings all the time. Maybe because I work with art people kind of say “whatever he is an artist”. But I am lucky they are easy going… I mean I am still washing my underwear by hand and hang them up to dry in our private toilet and I keep a lot of the crossdresing between me and my partner… but I like to introduce little by little looks that veer from the norm. A nice thing to do is watch movies or series together with them that introduce themes of sexuality, etc. Schitt’s Creek series was a good one, very light and fun, and works as an educational thing as well to open their minds. Talk is always nice, I think we need to be clear with the other. If it’s important to you to let your parents know what you are up to, just introduce the subject… in a natural way. Depending on their reaction I think is not worthy to push the boundaries with them. Different strokes for different folks and everybody can live their lives apart from each other with no problem I guess…

Gust March 02, 2021

That is very unfortunate. To cut our parents out of our life is something we should never do, what we can do is accept them the way they are. After all they come from an extremely conservative era. My situation went completely down the hill as my wife decided to end our 16 years marriage and took the kids. Why? Obviously I’m a freak. Well, there are those who are able to see the world in full colours and there are those who only see black and white and place themselves to the centre of it all. Unfortunately, the majority of us belong to the black and white side.

Ivo February 26, 2021

Thank you all for your kind words and support. It’s definitely a complicated scenario to be in, but what I do know is being true to myself is the most important. I have accommodated peoples comforts by dressing “normally” for far too long. We have one life to live, and living for others should never be a consideration. If a woman can wear jeans, t shirt and no makeup, then I too should be able to wear something as basic as leggings and foundation without offending anyone. That’s just my take on it.


Nathan February 22, 2021

Ally good point. He could wear less provocative clothes, like womens jeans and shirt light make up ( i wear every day) and no one knows. Question? Who is in those pics ? Beautiful

Get ur lingerie on!

Stevie February 21, 2021

Hi Nathan – well you’re certainly not the first to not meet the criteria for suitability deemed appropriate by your other’s parents. In essence though, what business is it of theirs? Given a little time, I’m sure they’ll come to realise how happy you make their daughter. Far better their daughter is with someone as sensitive as you than someone abusing her. They’ll probably take a little time to get over the shock of the way you presented to them. That’s not necessarily your fault, but the world still has its powerful normative ideals. I’m sure the happy times their daughter spends with you will filter back to them via her and they’ll come to realise how lucky she is. In the meantime, if you are going to see them, why not accommodate them a little? Wear jeans, a T-shirt and no make-up. After all a lot of women dress just like that a lot of the time. It’s just that they wear them over different shaped bodies to ours. How you dress is your business and the whole world thinks differently about different things. What’s important is the loving relationship you have with your other. In time, her parents will come to appreciate that and forgive anything else they might see as a little peculiar. With love Ally x

Ally February 20, 2021

It’s sad that they are pressuring their daughter to make a choice that goes directly against her happiness. I am happy she chose you and I hope she continues to support you.

Scott February 19, 2021

I am so sorry to hear that such a terrible thing happened. I can’t imagine how you must have felt afterward but I do want you to know that so many of us out here have been where you have been and I am glad to hear that you don’t let the opinions of some awful people affect who you are and how you live/express yourself. You are beautiful and amazing as you are. You provide guidance and advice to others and allow people to fully express themselves as who they are. You are loved by those close to you and by the members of this community who are so in your debt. Thank you for sharing your experiences with us. Please be safe

Joseph February 19, 2021

I am so very sorry that after you put yourself out there to show the true you, her parents shot you down. It must have placed a big strain on your relationship. Crossdressing has been placed into the same categories as gay and trans. Although a number of transwomen start out crossdressing, it’s not what happens to the majority. How you live and dress should be a very personal journey but the world is still controlled by conservative types who got a flat on the road to enlightenment in 1950 and refuse to get out the spare and move on. Keep doing what you do and be happy. As Ricky Nelson sung in Garden Party. " You can’t please everyone, so you gotta please yourself."

Steve February 19, 2021

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