A fellow blogger recently asked her audience for ideas on how to tell her fiancée about her crossdressing. The sense I got from the post was that she was looking forward to her fiancée’s absence – going away to school – because it would allow more dressing opportunities. They have been together for years and this “hobby” as she calls it was still a secret between them.

As I mentioned in my comment on her blog, my answer was longer than her post and would be better suited to being a blog post of my own. So here I am. And this is the advice I would give her:

I am certainly no expert on all this stuff, but I do have some limited experience of my own as well as discussions with fellow t-girls to draw on. I have always appreciated well-intentioned advice given without ego and without expectation that it would be followed unless I saw fit. I offer you my thoughts in that spirit, for you to use or discard as you see fit. So, here goes…

Trust is Critical

It is a mistake to be in a relationship and look forward to the times when you are free and she is busy so you can carry on activities which you hide from her. Trust is the most important thing in a relationship, and while many girls tend to fear the reaction their girlfriends might have to their crossdressing, it is often the lying and hiding that causes the most offence.

That is not to say that most women would find crossdressing acceptable. I would think that the vast majority would run screaming from the room. But some might come back once they had time to digest it, and others might be willing to tolerate it with certain restrictions.

Such are the odds that encourage many t-girls to simply not tell. But, that’s a big mistake.

First, there’s the trust issue, and if she finds out on her own or you decide to tell her years later, the biggest obstacle will be, “How could you keep this from me all this time?” It is not fair to enter into marriage with her while hiding something like this. She should be allowed to make an honest choice. Remember also that if this blows up years down the road, there will often be children involved or serious money issues. Not good at all. Better to get the crying out of the way when you’re young and can start again.

Hiding is Bad Too

Also, I am a firm believer that hiding this eats away at you. You’re deceiving the person closest to you, you’re under pressure not to make a mistake, and you are constantly reminding yourself that you are not loved for who you really are. It will wear you down and you will not be happy.

You Only Need to Find One Person – And You May Already Have

So, my first recommendation is to do some soul-searching and come to terms with how important crossdressing or transgenderism is to you. If you can live without it, you’re probably going to be happier doing so. But if it is an integral part of you and not just a hobby, then you have to accept that your pool of potential mates has shrunk by over 90%. The good news is that you only need to find one person! And it might even be the person you are with now…

If you do it right, you may find that you can convince your fiancée to at least tolerate your crossdressing. You may have to compromise and it may take some time, but you may be able to work it out.

Gentle Disclosure

Halloween is one of the most convenient tools we have for breaking this news. My suggestion is to find a costume party that none of your friends will be attending. Make plans to attend, say a month in advance. Then, make it clear that you want to go as a girl. Even suggest that she go as a man. Now you have that month to enlist her help buying a dress, shoes, stockings etc. for your costume, (all from places that accept returns) and try these things on for her at home. See how she reacts and you will have a good idea what you’re up against.

If she’s not weirded out by the whole thing and compliments you on how you look, you could sheepishly admit that you like the way it feels, and you always wondered what it would be like… slowly, carefully, one step at a time and see how far it goes.

However it goes, eventually you will come to a place where she did not expect to be, and probably doesn’t want to be. No one really wants to be in a situation where they are social outcasts, or hiding a secret that, if found out by the community, would make them social outcasts. You may be in a position where you can’t walk away and leave it behind, but she is likely not. Unless she is a rebel, kinky, or an admirer of our kind, the main thing holding her is her love for you. The weighing of this love against her feelings about your crossdressing and her own sexuality and social standing will determine what she does. But she should have that choice.

Good luck!

p.s. Perhaps an even better source of advice for those of you pondering this question can be found at Gabrielle’s myCDlife