Dear Gabi, I’m Having a Hard Time With My Boyfriend Crossdressing

Dear Gabi,

I have been having a really hard time adjusting to my boyfriend crossdressing. He told me when we had been together for two months. It has been a year since he told me and I am still adjusting. Is it normal to adjust so slowly? I guess I feel that I’m not in a normal relationship, and I feel like I am not the only girl in the relationship at times. He is very manly all other times and I love him so much. We live together and he is amazing.

My Problem lately has been that I feel I am taking pictures for everyone on the internet to see. He posts them almost immediately after I take them. He says that he feels sexy when people comment them. Another thing is that I want to dress up in sexy outfits too, but he never asks me to.

Another thing that he does is anal. He loves when I use a strap-on on him. This is the thing that frightens me the most. He has told me before that he wants to know what a real one feels like and I am afraid he will like it to much. I grew up in a house where this kind of stuff meant you were gay. And even if he is bi it scares me, because I do not want to share him with anyone else. He said that he likes having sex with me way to much to ever go gay but what if later on in life he does. I’m so scared to lose him and he knows that so what if he does it behind my back. I have gone onto his account on his computer and I know it is wrong but the only porn he has is girls with dicks. I cried for three hours because I’m scared that he will want me to be that way. That seems to be what turns him on and I’m not like that. I know this is a very long post but please respond to it. I just need some advice. I am scared and need some comforting advice. Please Help!

In Love but Scared

Gabrielle HermosaDear In Love but Scared,

I can certainly understand the difficulties you’ve had adjusting to your boyfriend’s behavior and the sense of uncertainty it has left in you. I think it is important to point out that based on what you’ve written, the issues seem to be more with his behavior and sexual interests than with his crossdressing.

Although you are scared and seek “comforting advice”, I think it is in your best interest to draw attention to some important points rather than just try and provide a false sense of comfort. In the end, everything may indeed work out well between you both, and I hope that is the case. However, I believe you need to address some important things before that can become a reality.

Good communication is vital to the success of any relationship. That is true whether or not crossdressing or sexual preference comes into play. You should let each other know what is wanted, needed, and expected of the other. This needs to be communicated openly and honestly. I strongly recommend engaging in serious discussion about your concerns with your boyfriend.

Posting photos and feeling sexy
It’s not uncommon for crossdressers want to feel sexy (the same is often true for genetic women) and everyone enjoys getting compliments. There’s usually nothing wrong with that. It depends on the kind of attention that is being saught, received, and how you feel about that attention. If you sense there is more to your boyfriend’s posting pictures than he is letting on, you need to let him know how you feel and why.

Dressing sexy
If you want to dress sexy, don’t wait for your boyfriend to ask. Dress sexy and see how he reacts. He has expressed his need to feel sexy, remind him of your own need in that department. If you’re concerned that he is only interested in dressing sexy (himself) rather than seeing you dressed sexy, talk to him about it.

Sexual preference
It sounds like your boyfriend may be bisexual, or at the very least, bi-curious. This in and of itself is generally harmless, depending on his level of curiosity. If you’ve discovered evidence that your boyfriend’s “porn” interests are only that of other crossdressers, it might indicate that his sexual interest leans more toward other (crossdressed) men rather than genetic women. It might also just mean that he’s interested in seeing others like himself. It depends on what he gets out of looking at the photos. It might be a good idea to ask.

Monogamous relationships
If your personal interests are in a monogamous relationship, you need to communicate this with your boyfriend and make sure you’re both in agreement and committed to each other on that level.

Men (crossdressing and non) often have sexual fantasies that cannot be fulfilled by their partner. For instance, a man may fantasize about having sex with two women at the same time, or with a particular celebrity. Having such sexual fantasies is pretty common and does not necessarily mean they will ever be realized or even seriously pursued.

Personal discovery
When it comes to gender expression and sexuality, there is often an aspect of personal discovery involved. Your boyfriend may still be discovering his own preferences. Ask him if his bisexual fantasies go beyond just a curiosity. He may not be entirely certain yet himself, so if he has some difficulty answering, try not to press the issue too hard and give him some time to figure things out.

If he does express sexual needs that you cannot facilitate, you’ll have to decide whether or not you’re ok with him having other sexual partners and take it from there.

Going through your boyfriend’s account represents a lack of trust on your part. Your concerns are absolutely valid and understandable, but you need to be able to trust the man you love and share a home with. In return, he needs to be able to trust you. If you cannot trust one another, the relationship will not be very rewarding and most likely fail. Again, open and honest communication needs to take place.

In addition, if you are seriously concerned about your boyfriend doing things behind your back, that says a lot. Whether he has done something specific to loose your trust or if you’re just worried about loosing the man you love, trust is a very important element in any relationship.

Reaching an understanding
Every relationship has rules. They’re not always talked about, but they always exist. An example of a common unspoken rule in a monogamous relationship is that neither parther shall engage in sexual activity with others outside of the relationship. Take the time to discuss and establish a set of rules in your relationship. Make clear to your boyfriend what is and what is not acceptable behavior. In return, he should also communicate the same to you. It is important to reach an agreement that you are both comfortable with and can both realistically adhere to.

I understand that you love your man and enjoy the relationship on many levels, but you deserve to be happy and it sounds like right now, you are not. Rather than just continue in your uncertainty, hoping for the best, take action and start discussing the things that have been troubling you. Some of your boyfriend’s behavior clearly falls outside your comfort zone and you need to let him know how that makes you feel.

The success of any relationship comes down to love, trust, respect, honesty, good communication, and compatibility. I hope the two of you can reach an understanding and find the happiness you both deserve, whether it be together, or apart.

Related content: Dear Gabi Advice Column

Write to Gabrielle: Dear Gabi submission page


8 thoughts on “Dear Gabi, I’m Having a Hard Time With My Boyfriend Crossdressing”

  1. I’d like to add an additional thought to some sagely written advice, if I may:

    Cross gender identities are complex things – both for the individual who finds themselves living with such an identity and by association for those closest to them. Finding a workable balance in life can often be difficult in the extreme – crushingly so.

    What does your boyfriend want? Is it purely centered around the erotic for him, or does she desire to explore the world as a woman socially?

    For the writer of the original letter, what do you want? What are you comfortable with? Are you willing to have both a partner and a sister in the same person?

    The balance each of us needs is different, and the real question is whether a couple can come to a mutual sense of balance that meets the needs of both individuals well. That may mean sacrifices of things that both parties hold dear – but should not mean suppressing something that is real for either.

    In short, can you help each other grow as human beings?

    1. Thanks for the additional thoughts, Michelle. :) The transgender spectrum is so diverse – it is not possible to sum up all who fall into this rather general category under any particular set of criteria that is all-encompassing. That’s no news to many of us, but definitely useful information to those seeking answers. I’m glad you brought it up. The questions you posed for the the author of the letter are excellent.

      To me it seems as if the boyfriend’s interest in crossdressing is more sexually driven rather than that of self-expression or gender identity. Even though the main question was addressed as crossdressing, it seemed as if all the issues and concerns centered around sexual behaviors and desires. I’m hoping that others will chime in with more ideas, thoughts, and suggestions based on what they get out of what was written.

      I’d really like the author of the letter to get a healthy dose of useful and meaningful information as a result of her reaching out for answers. That’s me asking for more of you to please take a moment and add your thoughts, ideas, opinions, knowledge, and suggestions. :)

  2. Dear In Love but Scared,

    I am a genetic girl too, with a cross-dressing boyfriend. It is definitely ok to adjust slowly to your boyfriend’s cross-dressing. It is also ok for your feelings to go “up and down” as you go along. I love my guy, I am totally ok with his cross-dressing, but I too have the same moment of why should I bother to dress sexy. Sometimes I feel like he is more interested in his own reflection. We talk about it. I let him know I am in need of being “the pretty one” getting the attention. It comes down to give and take, I am ok with his dressing and he understands sometimes I want my traditional date with him in guy mode. Communication, communication, communication.

    As for the sexual aspect, I think we have things in common there too. Cross-dressing for my guy seems to be more of a sexual thing than a serious gender issue. At times he is all guy and at times he thinks and feels more like a woman, I think he is happy with who he is and I am too. With that said, there is definitely bi-curious talk in the bedroom. I am ok with. Again, we have talked about it. I know it is, for us, just talk and fantasy in the bedroom. I also know that if it were ever to be more than that we would talk about it, neither one of us would go behind the other’s back. Communication, communication, communication.

    My guy also likes to take pictures of himself dressed “en femme”. Again, I am ok with this. I feel, with most things in life…moderation. My guy has only posted a few pics, but I think I get the thrill of it. As a GG, to have men compliment you and flirt with you provides a powerful feeling. As long as it stays as harmless flirtation. We talk and we share. When he gets dressed up and we take pictures, it definitely turns him on a little bit more, and I get the benefits of that! So we are both happy.

    I’m not sure if any of this helps you. I am happy with my cross-dressing guy. We have a serious relationship, with the issues that any relationship does, but cross-dressing is not one. I know my guy is private about his cross-dressing, so it is a little secret we share, it is fun. Talk, talk and talk some more is what I say to you. Some of your issues seem like just regular issues…will my guy be faithful? Even women in relationships with non-cders feel unappreciated so why should they make the effort to dress up? Talk, let him know that just as an evening dressed makes him happy, and evening with him in guy mode makes you happy. If you get what you need you will probably be happy to give him what he needs. Let him know your thoughts on monogamy, and that it applies to hetero and bi-sexual feelings.

    Gabrielle has great advice. I read her blog all the time. I rarely comment, but since she asked today I did. I found her blog when I was looking to talk to other women who date cross-dressers. I started my own blog if you would like to check it out, just a few ramblings about some of the fun I have with my guy. I am still waiting for other GG’s to find it.

    1. Thanks for chiming in, Lynn! :) After that very well written perspective from a genetic woman’s point of view, I certainly hope more gg’s find their way to your blog. You offer such an intelligent and insightful take on things, being in relationship with a crossdresser, and a loving & happy one at that.

      About commenting, please, by all means, comment on anything that stirs ideas, thoughts, etc. that you’d like to share. This isn’t a transgenders only need bother commenting environment. I most certainly welcome, appreciate, and do not ignore comments left by non-trans visitors. :)

  3. First I would like to comment on the dressing and feeling sexy part. I would encourage you to do so what you think will make you feel good. I realize that as a woman society has imposed this weird beauty contest mentality that to be sexy a woman has to be the prettiest in the room. But as a community we are about rejecting societal conventions.

    In a general way, I would like to put two realities (realities for me at least) out there. There is nothing sexier than a group of women that feel good and sexy about the way they look. If you don’t believe me just watch girlfriends going clubbing sometime. You can tell the ones that feel confident in the way they look. They aren’t always the prettiest either, but there are no others that are sexier. Together girlfriends make each other even more beautiful.

    Second, if you dress sexy and feel good, you will look sexy. No one will be able to take that away from you. You should feel like the sexy one whenever you feel like and wherever you are. And whomever has issues with that that is their issue. The important part is that you feel good about the way you look. Once you have that, you can’t help but exude that you feel good about the way you look.

    I agree that you have trust issues. The best way to deal with these is to communicate them. You shouldn’t have spied on your bf’s internet activities. All that does is make you untrustworthy as well.

    Let me explain. You clearly didn’t trust your bf before you went out to confirm your fears. That is the only real issue. Did you feel better after your fears were confirmed? I doubt it, and I believe your letter confirms that. What if they weren’t confirmed, would have you felt better? I doubt anything would have made you feel better. Not finding anything would have made you suspect that that he was just covering his tracks. Because the problem is that you have trust issues.

    And the only thing spying on him does make you feel like you invaded someone’s privacy. Additionally you have to keep the secret that you did it or expose that violated your bf’s trust, which makes your bf suspicious of you. So it makes matters worse no matter what.

    The best thing to do when you have trust issues with someone is to simply tell them how you feel. That way you are just dealing with your emotional needs and you don’t have all that negativity hanging over your head. If you still have trust issues after talking about your concerns then you have a clearer path to what you need to do. And you can that with a clean conscience.

    I might have more later but I have to run now.

  4. If I may add a little to the excellent advice that has come before…

    As others have said, trust and communication are key. It may be that your boyfriend has found someone he can trust in and he’s still finding out who he is.

    Oftentimes, you find a crossdresser will ‘go off the rails’ when allowed a little freedom. I am not making excuses for his behaviour, but I am trying to offer some reasons as to why he may be behaving in a way he wasn’t before.

    The rollercoaster ride will stop… but where it stops depends on where he – and to a very large extent you – want to. Maybe he’ll get tired of looking at the porn and posting pictures, maybe he won’t.

    I hope it works out for both of you. It is scary and while it can seem like just you having to cope with what’s going on, there are sites dedicated to the partners of trans people (where no trans folk are allowed). Trans partners is one of them:

    Good luck!

  5. That is true Lynn. Acceptance is so weird for a (closeted) crossdresser it is like Christmas in the middle of a dream shopping spree. I know I ended up feeling more like a teenage or even preteen girl more often than not. When you do it alone there is no socialization, and the only mirror you receive feedback from is the one on the wall.

    It freedom of being out as a crossdresser to one just one person (maybe especially a woman) is like flying or free-falling. I have come out as a crossdresser to 3 women. It wasn’t until the third that I managed not to go completely over the top trying to be best girlfriends girlie with. Even though I managed some filter it was still hard not to let the persona that remained under wraps for so long not to explode all over. It sounds like In Love still has some moderation issues to addresses because the filter is really hard to instill from the crossdresser side.

  6. I can’t really add much other than to point out that the crossdressing was revealed relatively early in the relationship, at least as described in the original letter. I revealed to my GF very early on and we have been together 3 years since that time. I think the key, as has been pointed out, is communication.

    I applaud the original questioning letter, it takes a lot of courage to ask for advice and shows a desire to work on a potential problem rather than hiding it or pretending it doesn’t exist. Gabrielle’s response, as well as all of the subsequent responses, are also very good.

    I wish you both well and hope that you find the answers to your questions.

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