I know I havn't been here that long, and am not the most experienced person around, but I have found many ways that can feel safe when telling someone about your little secret!
Be careful who you do tell, make sure you are pretty sure they will be okay with it before you do, but here are some ways I have found.
To a Friend/Sibling:
Depending on the type of friend, this can be a confusing one to figure out. I am just going to assume it is someone you talk to quite a bit and know personally.
You can start by transitioning some conversation towards talking about deep personal stuff. make sure you are in the right mood for it, it can make all the difference.
I have tried this two ways, both seem to work alright.
1. "If you tell me your deepest secret, and I think it is strange enough, I might think about telling you mine". This can get them excited to know something about you, and you may even get to know them better too.
2. This is one I do more often, because I've just kinda turned into this type of person. When talking with someone you generally joke around with a lot, and like to have fun, come out by saying something like "I have done so many crazy things before, and I am starting to lose all my shame, because I just enjoy life too much. Wanna know something weird? I like to cross dress and I don't even care who knows it!" you can add more about being proud, and not caring if people mock you or laugh at you, but that is the just of it.
To your parents
This one, I can't say I did so well here. Because my parents found out by my close friend ratting me out. Here is how I should have taken care of it.
Get really personal with your mom or dad, just one on one. Talk about how you are feeling down, because there is something about you that you feel you cant talk about to anyone. Being your parents, they generally should love you unconditionally, and will want to know. Tell them that there is something built up inside of you that has haunted you, and you want to let it out somewhere that you feel you wont be made fun of for. Tell them about how you like to cross dress, and tell them how it makes you feel. They will likely be understanding when you come to them very softly, and are admitting a deep secret.
To a girlfriend:
This one is a little risky, and you may want to be prepared to lose someone close to you. This may be better in the long run, so you don't end up getting too attached to someone who is not going to be accepting of it. Now this person will likely be someone you are very intimate with, and like to share lots of deep things together. The one key thing about sharing deep secrets, is that you want to come off as being weak. If you really humble yourself, the person you are telling will usually have sympathy, and feel your pain. This is something that may be a big part of your life, but you have to hide it from everyone, so it can really damage you emotionally! If you show your soft side, and show that you are willing to open up to her, it can help you feel much better about everything.
To a wife:
(Yea I know I'm 18, but this is how I would do it if I were married )
This one can be the most difficult of all, so be very careful.
Maybe start by going a couple weeks, gradually starting to act generally more feminine, then approach her with,
"I don't know if you have noticed in the past, but I have a pretty strong feminine side to myself. Now this might seem a little strange, but to tell you the truth, it goes deeper than it looks. I like to cross dress! It is something that has always been a part of me, but have been too shy to show it.It is not just a phase, and I will always have this kind of desire, but if it bothers you enough, I will stop doing it, just for you."
The most important part is that you show her that you care for her more than yourself, which should at least strengthen your relationship.
If it turns out she really doesn't like that you do it, and does ask you to stop, maybe go cold turkey for a while. Then after a few weeks/months, tell her that you are starting to feel down, because you don't feel like you can express yourself the way you want. No one can be mad at you for how you feel, so she may even be understanding, and make exceptions.
The common theme here for the tl;dr, would be
-People can't be mad at you for your feelings
-Be proud of yourself
-Not everyone can be good to tell
-Let people know that you are still the person they have always known and loved
-Make sure you get in the right mood to how you are going to tell them, and try to transition the conversation in that direction
-Those who matter don't mind, and those who mind don't matter
I hope that at least someone got something out of this, and hope that being 18 doesn't lower my credibility, haha. I have noticed a large amount of threads about people wondering how to come out and tell loved ones. So I wish you all good luck, I know how hard it can be.
I have come a long way in the past month. I have told a few close friends and family. unfortunately, the 'secret' has spread like wildfire and most the people I know, knows about this. I am preparing to publicly announce soon on Facebook, so that at least I can clear it up and have them hear it from me.
I am happy with myself, and although most of my friends don't necessarily approve of it, I don't let them lose their respect for me, and I still show that I love all of them!