My boyfriend is a crossdresser, what do I do?

You’re likely feeling a bit shocked – after all, this is unlikely to be something you expected when you entered the relationship. Your boyfriend was probably wracked with fear when you first found out, and it’s likely he didn’t tell you himself because he feared that you wouldn’t accept his crossdressing. He may be both nervous and eager to share more details with you. Don’t let him go faster than you feel comfortable with. After all, he has been dealing with this for years and you only just found out.

You shouldn’t fear that you’re in this alone – It is surprisingly common for men to crossdress, at least occasionally. Some estimates say that roughly 5% of men are transgendered. There are many organizations that help wives and girlfriends, I recommend Tri Ess as a great place to start. They offer a supportive environment in which you can share your situation with other woman who are going through the same thing.

It could also be that you’re thinking about this a bit too much – if you have fun together when he’s crossdressing, go with it. Don’t feel like you need to conform to an outdated set of societal norms!

A great resource is a book written by Peggy Rudd called ‘My Husband Wears My Clothes’. I’ve included a link below. This book was written by a woman who’s husband is a crossdresser. Peggy provides insight, comfort and support for any woman who finds out that her beloved is a crosdresser.



Tags: , , ,

About the Author

A woman living in Seattle, enjoying the freedom to be who she is every moment of her life!

43 Enlightened Replies

Trackback  •  Comments RSS

  1. jerry says:

    its reallytough seeing a friendship dissolve just for that reason you are a real person and truly want to be honest but then they turn away and some wont even talk to you ….Is it because of their insecurities ??ya kno if the friend is a girl even tho your not intimate but the relationship fades or if its a guy .. Ithink guys feel threateaned to some extent altho they dont admit it Thing is you have been friends with them for a time sometimes for years ..THEN they find out a poof its gone Idont understand if you have a FRIENDSHIP no intemacy no touyching or flurting,,, just a good friend and all the sudden theyseem to view you as the plague BUT you ARE the same person go figure what’s up with that?? Hatred is not an option

  2. bonnnie kash says:

    hi my boyfriend is a cross dresser and has been for years, but i just found out about a year ago and i was shocked, hurt and embarrased. he only does it when he gets hi off of meth and then when he sobers up he always say he’s fighting demons and thats not him, so we need answers

  3. jerry carpenter says:

    Hey for all of you out there unlessyou have been there you just don’t know what it is like..
    i was born with cromozone imbalance or 2 sexed once you have been given an idenity by your parents …(instead of them letting you decide what you want they decide for you)that is what I have been delt .Not that I hate my parents they are good people my mother died from althzhimers but my dads still here It is they just did not know how to deal with it as we do today knowing what we kno about genetic structure … and there seems to be a more at ease responce to the issue . Whether you just crossdress or have been delt what I have It is getting better through education and understanding ,,,… dont give up on yourself ,,I never did

  4. Alicia says:

    Hi I`m Alicia I been cross dressing for a long time when I was 10 years old I started wearing my mom and sister bras and panties I stopped for a while but started again I spend a lot of money for clothes and women stuff then I say I am stopping I give it all away then I cant stop I start buying again with me I don’t feel I am male I feel female I don’t like getting dirty I sit to pee every time I was on hormones I been bisexual all my life but since I was on hormones I am turn on by men more then before my wife is ok with it she know I like men and lets me sleep with men when I want she is ok with it all she buys me clothes my panties its great well I was pretty lucky but I hope thing work out for you and wish you lots of luck Alicia

  5. Shannon says:

    My boyfriend came out that he was a crossdresser near the beginning of our relationship. I was open to it and thought it would bring us closer. He had been in a relationship for 15 years with the mother of his kids, and she did this for him. After finding out that he had cheated on me several times with her (because she was more accepting I suppose), I found it hard to do when he’d request it. I’ve always been more of a submissive girl, wanting a more dominant manly man. I do love him so much, but often wonder if I’m really what he needs. He’s asked to have a 3some with another man, and we followed through with it. He tells me he enjoys dressing up because it makes him feel sexy. I notice a big change in him whenever he’s looking fem. The way he walks, talks, and even looks at me completely changes. I feel so awkward at times. I have to play a role acting as if it’s turning me on, when in my mind, I just want to run for the door or make him stop. He means everything to me and his happiness is so important. I wonder if my discomfort should be addressed or I should leave him? Bringing another man into the bedroom was difficult. I only want one. I’m worried that maybe he finds me boring, or might be bisexual. It’s exciting having a man that is different from most, and I consider myself lucky. I just want the uneasiness to go away. Any suggestions are appreciated. We’ve been together 8+ years now.

  6. Elaine says:

    Hi Ashley,
    Thank you for your kind words. In fact, each time i think of talking to my girlfriend seriously, I felt embarassed. I don’t know why I feel such way. She always sees me as a tough guy. Maybe it’s becouse in my country, the people here are not really that open. I do agree with you. I will do my best and discuss this over with her seriously. Thank you for your encouragement.


  7. Vanessa Law says:

    Elaine, I would caution against trying to change who you are for her sake. It may work for a few weeks, or a few months, but I’ve heard of very few crossdressers who have “cured”. I would encourage you to find others in the crossdressing community you can share your experiences with, and to try to communicate openly and honestly with your girlfriend. I know that this may be difficult for her to accept, but life will throw even more challenging things at us, that will try the love and care we have for each other.

  8. AngelaMarie says:

    I had the same problem when thinking about telling my future wife at the time. It started when I was about five years old.I have always felt as though I was indeed a female ,so I started to dress the part.When I reached my thirties,I met a woman and I ended up engaged to her. She started me on pills that were supposed to stop male pattern baldness. It did work ,but it had more side effects that I wasn’t going to find out avbout tilll later on down the road.I found out later that the pills shre had been giving me were birth control pills. When I started growing breasts is when I confronted her and she told me the truth. She told me that she wanted the rest of my body to match my long slender legs. Sher got her wish ! I went from being 38-32-38 ,to a feminine 42-30-41 figure. I love the new me,I just wish it could have happened 20+ years ago !

  9. Vanessa Law says:

    AngelaMarie – I’m happy it turned out well. Sometimes I wish my wife were as supportive about me taking hormones. I would encourage you to see a doctor though, hormones can have other health risks, apart from the more pleasant side effects, such as larger breasts.


Leave a Reply

The Breastform Store