The When, Where, How and Why of Telling

When a person cross-dresses due to gender identity, there is a fundamental shift in their persona. Not only do they look radically different, but they are also perceived as a different person. This is very unsettling for those close to them and often difficult to accept.

We get our “sense-of-self” largely from those around us. We rely on the input of others for our identity: How they treat us, how they define us, and if we are accepted or not. We compare and contrast ourselves to others as well; how do they act compared to us, what level of education do they have compared to us, how does their career compare to ours, and especially what they look like compared to us. They, in turn, get their “sense of self” through input, comparisons and contrasts with us.

Someone who changes (even for a time) something as basic as their gender, changes not only how they are perceived, but also how others perceive themselves. A strong negative reaction to your cross-dressing by family, friends and co-workers has a lot to do with how the cross-dressing directly affects their identity.

If your cross-dressing is more than just a passing phase or secret sexual expression, and rooted instead in gender identity, then you may want to consider finding a way to give those around you a heads up.

Unfortunately, most disclosure happens through accidental discovery, and since there is usually no frame of reference to understand this unexpected information, the resulting reaction is usually negative. Most people think sexual affair, Jerry Springer, or worse. Although negative first impressions can be repaired, it is best to have a positive first impression. A thoughtful approach to disclosure, framed within a context that is understandable, has the potential of working out well. Please see the articles below about telling a spouse and children. The question you should ask yourself is, “Why do I want to tell?”

The when, where and why of telling someone about your gender identity issue.

Telling is by far one of the most scary ideas a closeted cross-dresser ever entertains. It goes against their very fiber and conditioning. For older cross-dressers (cders) they have trained themselves NOT to tell, so the idea of divulging anything is even more frightening.

There is a certain amount of control in having a secret. When you cross-dress in secret, you feel as though you have ultimate control over something very personal. No one else has input into what you are doing and therefore no control over you in this area. This has a very real appeal for those who feel as though they have no control over their life. If someone feels they are a “victim of their life”, then cross-dressing can be an escape from those feelings. You could be saying to yourself, “I may have no control over my situation, but I can always cross-dress.” If you tell someone, then that control is lost.

However, cross-dressing can be addictive, and so therefore how much self-control do you really have? Are you controlling the when, where and the degree of your cross-dressing, or is this compulsion controlling you? Although no one has control over you in this regard, do you really have control? If your thoughts constantly turn to cross-dressing to the detriment of your other relationships, then you have a serious issue with either your gender identity, or out-of-control sexual impulses. Either way, this situation will only get more extreme. Please consider telling someone you feel you can trust and begin the process of getting your life back. Too much of a good thing is too much.

Before you tell, ask yourself why you want to. If you are planning on living full-time in your new gender-divergent role, then telling them will more than likely be unavoidable. If this is a part-time expression (i.e.: cross-dressing) you will have more options on who and when to tell.

What are your motives? (Ask yourself the following)

  1. Do I want to “shock” them to illicit a reaction?
  1. Am I telling them only so my life will be more convenient?
  1. Am I hoping to distance myself from them? (i.e.: If you wish to leave your wife, but want to shift blame onto her by saying, “Hey I was honest, but she was not accepting.”
  1. Am I more excited about my new found freedom or path than how they will feel about it?
  1. Do they really need to know about my gender identity issues?
  1. Will it improve or degrade my relationship?
  1. How old are they, and will the information hurt them needlessly, or do they absolutely have to know?
  1. Am I trying to make it easier on them or on me?
  1. How much should I tell?
  1. Do they have a context in which to understand my words and feelings?
  1. Do I wish to be honest and open?
  1. Am I planning on blaming them for my “condition?”
  1. Am I in a rush? If so, why?

If you answered “yes” to questions 1-4 then you seriously need to rethink your motives. Chances are you have other issues that need to be addressed first, before you “tell all.” If y

If you answered “yes” to questions 1-4 then you seriously need to rethink your motives. Chances are you have other issues that need to be addressed first, before you “tell all.” If you want to shock, damage, or pay back someone by upsetting them with this news, then you should consider repairing the relationship first. If the relationship is over and you need to move on, then state your reasons clearly to them first why you wish to end your relationship. Do not make your cross-dressing a lightning rod for the relationship-frustration, and so the big reason to leave.

You need to sort out where your impulses are coming from. If this is just a sexual impulse, then you may want to address that reason first. Do you have a lack of intimacy with your spouse or significant other? Would you like to increase your intimacy? Perhaps you should address that first by seeking out a sex therapist, or just have a heartfelt conversation and clear declaration of your needs with your spouse or significant other.

Make sure your motives are sound, and the information you plan to share is within a context that is understandable. Try to put yourself in the shoes of that person and give only the information they are able to understand and absorb. Speak slowly and let them process what you are telling. Most people can relate to personal feelings. Most family members will listen to you if you talk about cross-dressing and gender identity in terms of your struggle. You can connect on feelings more easily than you can on clinical, medical or scriptural information.

You do not have to tell everything all at once; you can take your time. If they have questions for you, take your time and think about your answers.

Have realistic expectations. Don’t assume you will be vilified, nor should you assume that they will fully accept what you are saying. Your guess at how they will respond could be right on or way off. Prepare yourself for the worst case scenario if possible, but hope for the best.

If you plan on telling your spouse and your relationship is solid, chances are they will be more accepting or empathetic than not. If your marriage is rocky already, the news you are transgendered or a cross-dresser usually will not go over well. It could be the “last straw” and become the focal point of an already poor relationship. If your relationships are sound now, chances are this new information will be within the context of a good relationship. If not, the information will just be added to their “list” of why your relationship isn’t working. So try and shorten the “list” before you tell them.

The best time to tell is when nothing else is happening. Don’t tell on anniversaries, birthdays, Christmas, graduations, funerals, weddings or some other special event. Those you are telling will be the least receptive during these times. When you tell, make sure there is lots of time available to talk about it.

Above all give yourself time. If they are upset, let them vent uninterrupted. Remember the response they give first is mostly emotional. Validate their response and let them be emotional. You have had a long time to think about this, and they may be hearing it for the first time.

Consider talking to a therapist first.

A therapist can give you information about what you are going through in a clinical, yet emotionally supportive fashion. Some advocate having a therapist or knowledgeable friend present when you first tell. This may help to make your case, but could have the result of putting your family member or friend in an adversarial role. They may feel teamed up on and will want to defend themselves.

If you tell them on a one-on-one basis (alone), chances are they will have lots of questions for you anyway. After this initial “telling” they may want to seek out a professional or knowledgeable person’s opinion. At this point, you can bring in a therapist or recommend a resource to help them understand.

It is best not to start with, “I have a problem.” This will send up red flags and couch the information as completely negative. Instead, try saying, “There is something I want to share with you. I know I can talk to you about anything, and you will be supportive.” Starting off in this way should help to affirm your relationship and provide a positive context of trust. If the person begins to freak out at this point, chances are they will not be ready to hear the rest of your speech.

Take them through a brief background about your feelings. Discuss your struggles in terms of feelings. If they can see this is important to you and is something you need to share with them, they should be more responsive and ready to listen. They may even feel good that you trust them so much. Focus in on that.

You will not be able to control the reaction of others, but there are things you can do to help create the best scenario possible. Don’t be afraid to share your emotions and let them in.

Although we hopefully have given you some good advice, the response to “telling” is extremely varied. Some will be understanding or even supportive, while others will totally reject the information and perhaps even you. A relationship can become deeper and more fulfilling as a result, or end. There are no guarantees. If you are considering telling and decide you really want or need to, then count the cost first and decide if you are willing to pay the price. For many, the freedom and relief in letting someone in is worth the potential back-lash.

If the thought of telling is still too scary, start off with a person first who does not impact your life directly. A Stephen Minister at your church perhaps, or a therapist could be a good start. I would not go to your head pastor or deacon first. They have their own agenda and will not usually be concerned with you, but with how this will affect the church congregation. Choose someone you think will be open. Perhaps a clergy from a church in your area that is accepting of those in the LGBTQ community is someone you could talk with or will know of someone. Going it alone is never the optimal choice. You should be able to find someone safe to share this with who will be supportive. There is support for you out there. You are not alone.

Many congregations are becoming aware of transgender issues. As a starting point, here is the web site “Institute for Welcoming Resources,” a list of churches that are welcoming to those in the LGBT community. If one is in your area, they could be a good resource for counseling and affirmation: