10 mars 2009

My cross-dressing boyfriend feels uncomfortable when I cross-dress

I am a woman in a long-term relationship with a man who came out as a transvestite about two years ago; several years after we began dating. He is the only man I have been sexually attracted to, otherwise I am almost exclusively attracted to women. I am confused about my gender identity. I had some discomfort with this when I was a child, but eventually made peace with my body and the urges to express my male-ness almost completely disappeared. With his coming out as a cross-dresser, my desires have returned and I have begun collecting male clothing again, and wearing it in private. I cut my hair several months ago, and my boyfriend and parents had a fit.
My boyfriend is aware of my bisexuality, but my transvestism only comes out when I am drunk and it makes him extremely uncomfortable. My parents are neither aware of my gender nor sexual identification.
What can I do about managing my attraction to women, and how do I explain all this to my family? Do I have to?

Kay Wo

Hi Steph K,

Thanks for sharing your story with us at AlterHéros. There seem to be multiple layers to your post:

1. You’ve recently been experiencing some gender identity dysphoria that you thought you made peace with as a child (you managed to repress any urges to express your male-ness);

2. The coming out of your long-term boyfriend as a cross-dresser has triggered your own desire to start cross-dressing, so much so that you’ve begun to collect male clothing, wear it in private and cut your hair;

3. Your boyfriend and parents are not pleased with your expression of male-ness (e.g. it makes your boyfriend uncomfortable when he sees you drunk and wearing male clothing and he and your parents both had a fit when you cut your hair);

4. Your parents do not know about your gender or sexual identification and you want to know whether you need to come out to them;

5. You want advice on how to manage your attraction to women;

6. You want to know how to best explain all of the above to your parents.

Phewf! That is quite the list so let’s get started. Firstly, it is not uncommon for an individual to feel confusion regarding their sexual identity later on in life. This is especially true for someone in your shoes who can clearly remember having feelings of opposite gender identity early on in life as a child. What seemed like a successful integration into societal norms of femininity for you in the past has actually lead to repressed feelings of masculinity that have popped up for you to deal with now. Surprise! In all seriousness, it’s actually a positive thing that these feelings have resurfaced now while you’re still young and can work through them.

It is clear from your post that you still aren’t comfortable with your desire to express your male-ness since your cross-dressing only occurs in private or while drinking. This is understandable because you are essentially going through a coming out process. It is never easy to express who are when your expression doesn’t fit with what society – and let’s not forget what your parents and boyfriend – expect of you. You should know though that like sexual orientation, gender identity is not something that can be altered, even if we wish it to. Your feelings of male-ness are not going to go away; if you repress them, they will undoubtedly come back later but stronger than before (like what happened when you tried to manage them during your childhood). What you can try instead is to explore this new male identity in a situation where you will not be judged for it. You can continue cross-dressing in private to figure out your personal boundaries but it would also be helpful if you can find an outlet to express yourself in a non-threatening context. Try going on online chats to reach out to others that have gone through a similar experience (see online chat sites below). From here you can determine whether or not transvestism is enough to sate your feelings or if you think that they are further reaching into the realms of transgenderism.

Though you did not express this in your post, it is common for someone in your position to experience feelings of resentment towards his or her partner due to a lack of support for this new desire to cross-dress. It may seem logical to you that because you were so open and accepting of your boyfriend’s transvestism, he should also be able to provide you with the same treatment. His discomfort may be hurtful to you, especially when you really need his support right now. Firstly, you truly deserve kudos for being so understanding when your boyfriend came out to you with his transvestism, especially so late in your relationship. However, as reasonable as it may seem to expect him to be as accepting of you as you were with him, it doesn’t always work this way. When your boyfriend fell for you, he fell for you as the woman he perceived you to be. If he identifies solely as straight, seeing you as a man is probably really jarring for him. He may care for you deeply, but he can’t control the way he feels when such a fundamental part of who you are (your woman-ness) changes or goes away. So when you wear male clothes or sport a short hair cut, he most likely can’t help but worry that you might be changing into a person that he physically may not be attracted to. As unfair as this seems, it is a reality that you will probably have to face with the changes you are considering making.

When it comes to your gender identity, it is likely that your parents have known about your tendencies to “act more male” ever since your childhood. But since you were able to repress this behaviour, they probably chalked it up to it being a phase that you “thankfully” grew out of. This could explain why they were so quick to have a fit over something as simple as a haircut. So you have to ask yourself, how important to you is it that they know about your gender identity and sexual orientation? How close are you with them? How involved do you want them to be in this sphere of your life? For some people, they never have to come out to their parents because they don’t share this part of their life with them. It’s just not something they talk about whether it’s because they don’t think that their parents can handle it, whether they’ve grown too distant physically or emotionally apart or simply because they just don’t want to. For others, it is important to have their parents involved in their lives, especially when it comes to life changes like marriage and children. So where do you fit in this spectra?

If you do decide to come out to your parents, be sure to do it when you are ready and comfortable enough in your own skin. The coming out process, whether it is for sexual orientation or gender identity, is something that an individual goes through on a personal level but once s/he decides to include his or her parents, her/his parents will also have to go through a coming out process of their own. In your case, they will need time to adjust and learn how to be comfortable with the fact that their daughter feels more comfortable expressing herself as a man and prefers to date women. They will also have to learn to be okay with talking about your new gender and sexual identity to their friends and with your extended family. Your parents would essentially be running the risk of rejection from these important people if they accept you and speak openly about you. This isn’t to discourage you from coming out, but you must know the risks and the consequences that come with it. Overall, it is a lot to take in, especially for individuals from your parents’ generation and older; for many parents, they fear what they do not understand. Keep this in mind throughout the process: acceptance can take time for even the most sexually open-minded parents so keep your cool, explain what they don’t understand and maintain your patience with them because the changes will come slowly, not overnight.

There is no magic coming out formula that is available for you to follow but there are some general suggestions. Firstly, choose a time where you are doing something casual and where you’ll have time to discuss everything through. You are an adult now and as much as your parents’ opinions matter, it’s most important that you know who you are, what you need to say and that you stand your ground. Also, be sure that you are able to make an exit if things get heated, so that you can give them a chance to cool off and ruminate for themselves on their own time. Again, the coming out process can take a very long time, possibly even longer for them than for you. So be patient with them and be as honest as is comfortable for you when answering their questions.

Lastly, regarding your attraction to women, it sounds as though you’re not 100% comfortable with being in an actual relationship with a woman. Dating your boyfriend has afforded you the opportunity to put off exploring your same-sex desires. Keep in mind that attraction should be something that you enjoy exploring rather than something that needs to be “managed”. Since you are in a heterosexual relationship right now (assumingly monogamous), you’ll either have to continue holding off starting any romantic relationships with women or discuss with your boyfriend if he would be okay with opening your partnership with him to another woman. This is a whole other can of worms that you don’t necessarily have to address before all the other points discussed above so perhaps you can write in again if/when you reach this step in your relationship.

A lot of stuff has been addressed in this post and hopefully, it helps you figure out what you want and what you need to find happiness. If you live in Québec or in the Ottawa Valley, you can always call Gay Line to speak to someone one on one about all the issues brought up here. They are a listening service that has trained volunteers available to help you discuss not just matters of sexual orientation but also trans and a variety of other topics (contact info below). Another group called ASTT(e)Q (Action Santé Travesti(e)s et Transsexuel(le)s du Québec) is also available for information regarding transvestism, transgenderism and transexuality (see contact info below). If you live outside the Québec area, you can seek the services from some of the resources listed below. Good luck and please write us back if you have any new revelations or questions to share.


K-Wo for AlterHéros





Gay Line

Available everyday from 19h-23h5

514-866-5090 (Montréal area)

888-505-1010 (Québec region outside of Montréal)

ASTT(e)Q (Action Santé Travesti(e)s et Transsexuel(le)s du Québec) – 514-847-8850




Toronto Area Gays and Lesbians (TAGL) – (416) 340-0330

7 pm to 10 pm, Monday to Friday

Fabulous Youth of Halton -(905) 469-1859

Serving Acton, Burlington, Georgetown, Milton and Oakville

London Gay Line – (519) 433-3551

In the London, Waterloo, Kitchener and Windsor areas

Gay Line Ottawa – (613) 238-1717

In the Ottawa area

LGB Line – (613) 531-8981

In the Belleville, Cornwall and Kingston areas

Lesbian, Gay Bisexual Centre – (807) 343-8813

In the Thunder Bay and Northern Ontario area





24-hour support/crisis line operated by the Calgary Distress Centre to support sexual minority and questioning youth (1-877-688-4765)



Social, educational and support group for crossdressers based in Vancouver

And last but certainly not least, here is a very good listing of cross-country services, in case you are in a different region than the ones listed above: