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
 

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.

Communication
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.

Trust
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.

 
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Her original message has been broken down into small sections so that I can address each point directly:

I have so many crossdressing questions that I don’t know how to address. My boyfriend is a crossdresser…

You’re not a lone, Anna. Crossdressing is very much a mystery to most people. I don’t have all the definitive answers (no one does), but I’d be happy to offer my personal insight and opinion.
 

We dated probably a year before he told me, by then I was so in love with him that I couldn’t leave, but didn’t like it. Leaving would mean I was shallow, that our love wasn’t real.

Not all couples are going to be successful because of a variety of issues. When a breakup occurs, it does not mean that the love felt by both wasn’t real. It usually just means that two people were not compatible enough to remain together. Breaking up is never easy, but it is sometimes necessary and healthy to do so when differences are greater than the personal tolerance levels of each or sometimes just the one.

So I let him do what he did. Prayed it was a phase, but it ate at me. So after three years we split up, but two months alone was all it took for me to actually grasp that it’s just who he is. It doesn’t mean that he’s gay and that he’s going to leave me later in life for a man.

Crossdressing is no more a phase than being right-handed is a phase. I’m glad you worked out that it is indeed simply who your boyfriend is.

Some crossdressers are gay, but it works much like like it does for non-crossdressers. If someone is straight, it is highly unlikely that they will magically turn gay (or vice-versa). If your man is into women, it has nothing to do with his crossdressing, but rather his sexual orientation.

It’s no different than me being a tom boy and wearing athletic shorts and t-shirts some days than his days of needing to wear heels and a blouse.

It’s a lot like that, yes, but a little different. There is typically a need for feminine self-expression that triggers dress-up time. I prefer to remove the word “feminine” and just explain it as a need for self-expression, period. That is a need we all have, regardless of how society sees our personal preferences in appearance and attire.

We want it to be a secret from our families. I don’t think his would understand in the slightest. But what happens if we have children? They will need to see Matt as Michelle, he’ll need to do that in front of them. But eventually, especially as a toddler, they’re going to say something about Daddy wearing Mommy’s clothes… I need children though, being a mom is a strong a need in me as being a cross dresser is to Matt.

My personal take on crossdressing and children is to allow the children, from a young age, to know the truth about their father. Treat it as an aspect of everyday, normal life and your children will grow up learning the truth about crossdressing rather than being taught the lies by our not-so-understanding society.

You concern seems to be in the kids mentioning how Daddy dresses to others, and that is understandable. Kids will be kids and you cannot control everything that comes out of their mouth. You can however, lay down the law and enforce it. If certain things are not to be mentioned outside the house, that needs to be made clear to your children. I think the main factor that comes into play is the level of discipline you choose to assert with your children. You can minimize the chance of the wrong thing coming out of your kid’s mouth by reinforcing negative actions with consequences and punishment. Even so, there will always be a chance that something is mentioned and the secret gets out. You need to ask yourself if that is a relationship breaker. Only you know the correct answer to that. Also keep in mind that times are changing. Maybe your parents/in-laws will always be of the same mindset they are now, but the the next generation of youth will be far more open-minded and accepting of differences and gender expression.

How do you cross dress in public? Is this only a thing in your house? Do you go out but pretend Gabrielle and Mrs. H are just friends? We live in a town of less than 5,000. Half the town thinks we should chase the gay people out, I’m worried that they’ll never leave us alone if someone found out.

Crossdressing in public is something I’m only starting to do myself. Unfortunately, like yourself, I also live in an area that is not very open-minded (or crossdressing-friendly) and therefore put myself in danger every time I leave the house en femme. Because of this, I am taking it slow and being cautious. I may never be able to maneuver in public (in this area) with the freedom I’d like, but I will not be kept locked in my house out of fear. Depending on how things go, moving to a more open-minded location might be necessary. We all have a need for freedom in our lives. If I cannot find it here, I will go to a place I can. This is something I have discussed with my wife. She has a lot of family here that she is very close to, but understands that she can always visit (as can they) should we relocate.

My wife and I have not yet ventured out into public together while I’m en femme, but it is a topic we recently discussed as that day draws nearer. Rather than show any romantic signs of affection, we would behave as if we are two good friends. There will be no hand holding, kissing, etc. The idea is to draw the least amount of attention.

Do you shave your armpits, legs and arms? Matt [boyfriend] wants to start, and I will get use to that as well, but part of me feels like that will mean “Michelle” is taking away parts of Matt from me.

From the neck down, everything gets shaved… with one exception. I’ll leave that to your imagination. :) The first thing I started shaving was my legs. My wife used to love my hairy legs so it was something she had to adjust to. Then came the arms/hands, then armpits, and finally I shed my facial hair. The facial hair was the hardest for her to see go, but she understood my need to not be the bearded lady when I dressed. For a while, she looked at me and asked “where has my husband gone?”, as she adjusted to it. I had facial hair for several years and looked very different without it. She loved me enough to allow me to shave though. It was something that I discussed with her for a long time before shaving (each area) and only did so after she seemed willing to give me her blessing. Though I did not need her blessing do change anything about my personal appearance, I personally felt it was important that she be comfortable with it before doing so. Though how I look has changed some, I am still the same man my wife fell in love with so many years ago and she knows that.

Does your wife ever have days where she says, ‘sweetie, I love Gabrielle, but today, I just need Gabe.’? I’m worried I’ll have those days, and I don’t want to hurt Matt, but I want to ever resent this either! Is that being selfish?

Every relationship has some give and take in it. Couples routinely agree upon compromises in order to maintain peace and contentment. When Mrs. H. wants Gabe instead of Gabi, she lets me know. I don’t resent her for it nor do I take it as a selfish request. Since coming out to her, she has been supportive, understanding, and not stood in my way when it comes to crossdressing. If she wants some quality time with my man-side, quality time with Gabe she shall have. Likewise, when I need some time to be Gabi, she also understands.

The key is to be completely open and honest about these feelings with each other. How much time is spent in guy-mode vs. girl-mode needs to be discussed and worked out among the two of you. You’ll both need to be very respectful of each others feelings as you discuss this – that should go without saying. Remember – you’re in this together and how one of you looks/acts does affect both.

I love him, in a way that nothing will ever stop me from loving him. I don’t want Matt to ever feel like because it took me a while to fully accept that one day I’ll get sick of it and leave him. Advice on how to reassure those fears?

Life is change. How a person feels about another person today may not be how they feel about them tomorrow. Matt’s crossdressing is but one of thousands of elements in your relationship. There is no way to reassure him that you will not get sick of anything about him and leave… unless you’ve got some insight into what the future holds. Because most people do not, this simply cannot be done with any certainty. I think the best you can hope for is to just let Matt know how you feel about him, period. Neither one of you can predict if what makes you happy today will make you happy for all of time. You can however, choose to maintain open, honest communication and agree to work out your differences. Good communication is the key to any successful relationship.

Anna, it is commendable of you to want to learn more about the realities of crossdressing rather than just treating it like some kind of personal defect in the man you love. If there is enough love, respect, honesty, and a commitment to good communication, I think the two of you will do just fine. How ever things work out, I wish both of you all the best in life.

 
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