Telling my new Girlfriend

So me and my old girlfriend broke up over the summer and I have recently started dating somebody new. We have had a couple of conversations about our lifestyles and belief systems and everything seems to click perfectly. The only thing is that I haven't told her about my crossdressing yet and I don't really know the best way to come out to her. With my ex I didn't really have a choice in the matter she kind of just stopped by unannounced one day and caught me. She was totally supportive and came from a way more conservative family but for some reason I am still worried about coming out to the new girl. Any tips would be nice,
Thanks in advance,
Kaylyn

Paint your nails, when she ask, it will give you an opening. To talk about your dressing.

...or open a conversation about gender issues.

If she figures out that you understand the feminine side of things, it won't be such a shock when you display those traits.

- MM

Looks like the ball is in your court my friend. My advice? Just be open and honest when you talk.:)

Depends on how serious you think this might get. I was already in love via e-mails and phone calls when I first met my wife for a weekend at the beach. I underdressed,, because if things, umm, progressed, then she needed to know right away.

But if this seems more casual, then you have two choices; 1, tell her and tell her SOON, or 2, save it until you decide you want to break up with her and then show up for a date dressed.

Jaye

i would think it best to confess in the early stages of a new relationship!
be honest and upfront with her so that she knows from the beginning.
this way she can make a decision and nobody gets hurt.
it's too hard of a secret to keep, and not fair to either of you.
wishing you the best and good luck!! :)

Agree with Paula above - tell her now. Find a quiet moment (well, a bit more time than that) alone with her and just be honest. Tell her that you are revealing a huge secret because its something she deserves to know before the relationship progresses further. Then give her a chance to think about it without pressure.

Have a friend who's dealing with this. Tell now and demonstrate honesty but risk alienation? Or tell/get caught later and demonstrate dishonesty and subterfuge? I think the question you have to ask yourself at this stage in your life is, "Do I want a girlfriend who isn't supportive?" I would tell and let the cards fall where they may. But I'm not in the situation you are...

I totally agree with Bridgette on this one...

I think you should tell her now rather than later. Yes, it may cost you the relationship, but better to see it come apart now than in, say, 30 years... And if she can't understand you or your lifestyle, you should consider yourself lucky to have gotten out early when the pain of the breakup is at least of a shorter duration if not in intensity. On the other hand, if you find her to be supportive, you've got yourself a real winner that you know you can count on for a long, long time.

I'm not saying hide the fact that you are female on certain levels.. I'm saying find a way to ease into the information rather than just blurting it out.

As you bring up topics and have conversations, it should be evident to you if she is receptive or not. Taking this kind of approach allows you to 'dip your toe' into the topic rather than going straight for the Cannonball in the pool.

I get why some of our sisters say bring it up now.. I mostly agree. It isn't the information, it is how you present it. It is a variant on the 'fast or slow' method of removing a band-aid.

I would *never* advise hiding important facts like gender identity (or other relationship affecting issues). If it is part of YOU and you need your partner to ACCEPT that, then you need to find a way to expose that without endangering yourself. You also need to have that figured out before you are in the 'committed' stage of your relationship.

Best of luck, and I hope things work out!

<3

- MM

I don't think that waiting is entirely a bad thing. Not everyone wants to advertise it right away especially with some of the terrible reactions I've heard about. You can determine if she would be receptive and could be accepting. I would say that it wouldn't be good to wait too long though. Even if it may not be entirely honest, I think if she cares for you and can empathize, it would easy for her to understand why you aren't completely upfront about things.

in my signature is how i did it. You can't leak it, just tell her.

Quote:

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Originally Posted by paulaprimo

i would think it best to confess in the early stages of a new relationship! be honest and upfront with her so that she knows from the beginning. this way she can make a decision and nobody gets hurt.

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Quote:

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Originally Posted by jenna116

Agree with Paula above - tell her now. Find a quiet moment (well, a bit more time than that) alone with her and just be honest. Tell her that you are revealing a huge secret because its something she deserves to know before the relationship progresses further. Then give her a chance to think about it without pressure.

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I'm a big supporter of full disclosure as early as possible in a relationship - and in the case of online dating, before you actually meet for the first time! - so I agree 100% with both Paula and Jenna above.

Yes, you run the risk of your new girlfriend walking away from the relationship, something you're undoubtedly worried about, but the longer the relationship develops, the deeper it gets, the greater that fear will be... so when would you tell her, in a few weeks, months, years?!

Wouldn't you rather have a girlfriend who supports and understands you, who loves "all of you" from the beginning, rather than dressing behind her back and trying to explain it to her later?

As Jenna says, arrange an evening when you can be together, just the two of you, and tell her you have something you need to share with her, something important, something you don't feel it would be right to keep from her.

I think it'd be a good idea to have some photos of Kaylyn available if she shows interest, but do take it slow, move at your girlfriends pace, don't make it seem as if she's being forced to make a decision about anything, you're just sharing a very private and intimate part of yourself with her.

Good luck to you both!!! :bighug:
Paula

I had the same problem once. My solution was to wash a pair of black-seamed nylons and one of my bras (of course my favorite) and leave them hanging in the bathroom of my apartment.
Anyway, she came over and we went on like normal and then she said she had to use the bathroom. I said, “Sure, go ahead.”
When she came out she had a strange look on her face and I said, “My turn”.
When I came out I said, “Ah, sorry about that. I guess I forgot to put them away.”
Make a long story short, she asked me to dress for her and everything turned out just fine.

Funny you should ask that. My last girlfriend passed away at the beginning of the year. We were actually more like brother and sister, or sister and sister. She was the main reason that I wound up were I am today. I call it gender fluid.

When she died, it turned my life around 180 degrees. It was actually more than that. I had a new life, was pretty much retired and I was in a position to do whatever I wanted, whenever I wanted. Since she was such a catalyst in my finding out this side of me, I promised myself that I would continue and do so like I had never done before. I also decided that if and when I met someone that they would know and I would continue to be Cassandra whenever I could. If it meant that a relationship didn't flourish and move forward, so be it. It was very different indeed to find that at this time in my life, I actually enjoyed being alone and would not compromise my life just for the sake of having a girlfriend.

So about 18 weeks ago I met a really nice lady. We really hit it off in a big way. And yet I am being cautious with my heart and what I have. I'm no longer working, struggling to pay bills, but at the same time I'm not really wealthy. It's surprising that I am being careful about this instead of just falling madly in love. Why is that?

After a few weeks, I told her about some of the things that went on in my previous relationship/lifetime and about my dressing up. She was okay with that and the only thing she said was "You're not going to get all transgendered on me, are you?" And although it wasn't until last week that I actually dressed up in front of her. But she's been the source of a great deal of encouragement. She told me to get my ears pierced and I did. That is just awesome. Not only can I wear real earrings, but I can wear some of the ones that my girl had bought in Mexico when we vacationed. I had some of her rings re sized too. We went for pedicures last Monday and afterward, she painted my fingernails and toenails. And then she did my makeup. Of course, before she did any of that, I put on a pair of capris and a blouse along with one of my wigs. So now, I've been dressed in front of her 3 times since last Monday. It's very very awesome to say the least.

I am sure that in the near future, not only will I be going out more in public, but we will be going out together as well. The whole experience with her has re-ignited my desires to dress and spend as much time as I can in girl mode without losing my guy side, which I actually enjoy quite a bit. Maybe she's just going along with it because she's needy or desperate or will have a hand out at some point. Who knows. In the meantime, I am thoroughly enjoying this.

If this relationship doesn't work out, it won't change anything. Any woman I meet from this point on, will know and Cassandra will be a part of our lives. Why? because it's part of who I am. And I'm going to be honest about that an enjoy my new life. After all, I owe someone that and it's debt that I can only repay by being true to myself. I feel bad for those on here who have to hide, and I understand why.

So yeah, if I rambled a bit here, sorry. Just be honest, and true to yourself. Something I just thought of and it should be an obvious thing to tell woman. You're obviously interested in pursuing a romantic relationship with a member of the opposite sex and that's all that should really matter.

I haven't a lot to add other than a question or two. How important is it to you at this moment in your budding relationship? Are you seeking a long term relationship, and do you want your partner to be supportive of you, as your last gf was, or more so? If this relationship doesn't endure, will you mind that she knows this information?

I'm not asking these questions to discourage you from coming out...quite the opposite. But I think you need to give these kinds of questions some consideration beforehand.

within a week of meeting my S/O, I told her. we were laying in bed, she got up and went to the bathroom, I picked up her panties and put them on. when she came back and saw me she just smiled and said "well thats interesting". It progressed from just under dressing to dressing and going out, shes very supportive.

Be honest and sincere in sharing your story with her. Listen carefully at her response without interrupting. Let the chips fall where they may. Try very hard not to impose your feelings on the subject onto her. She has the right to have her own feelings, whatever they may be.

Good luck!! :)

Tell her now, be fore you get any more emotionally invested! If she's ok with it, great! Move forward in the relationship. If she's not, then at least you know before it got to serious. Getting caught, or her stumbling upon your "stash" seldom ends well.

I'd always adopted the sooner rather than later approach when it came to disclosure. For me it was the point where a relationship went from casual to committed and mutually monogamous. I could never let anyone develop deep feelings for me without knowing. Being full-time it's no longer an issue these days.

having been married to an unaccepting spouse for a very long time this would be my advice. I would simply tell her soon that this is a part of you, explain why you do it and have that conversation. I think it is fair to her to get deep into why you do it and what the expectations would be if you stayed together. That allows her to make her decision. I told my wife early on but we never discussed why or what my expectations were for it and that has caused a lot of issues.

Not to pile on, but tell her now before you are so emotionally invested that you will hide who you really are. Trading your true so self to make her happy rather than making both of you happy.

Yes to all of the above. And, it's all about being honest with yourself and her together.

I also wonder if the longer you wait, the harder it will be to describe as the anxiety builds.

All the best,

Kate

Hi Kaylyn

I would like to skip a few steps forward if you don't mind. Say you tell her and you find her supportive, I suppose that will be great for you. I just want to warn you though that you cannot build a long-term (and possible future marriage?) on this fact alone. Yes, having a supportive wife is, I suppose the holy grail for crossdressers, but remember there are an awful lot more important things to consider when taking a partner/wife for a long-term relationship than just the fact that she has no problem with your dressing. I always get concerned when I hear people say "Marry her!" when someone comes out and is accepted by his girlfriend. Always remember that it is more important to look past that and look for a partner you share commonality with on more important issues such as goals/morality/spirituality/child-rearing and education/having (non-CD) fun together. You know a soul-mate. Don't marry someone just because she's into your dressing. For me, personally, I'd rather fight my wife on CD issues than on everything else!

Reading my wife's take above, I'd add stay away from surprise dressing and/or showing photos immediately. Let it sink in a bit first, too much info all at once can be a bit much to stomach. I wish I knew this back then, but then, I'm not sure it would have gone done well anyway.

Write her a letter, give it to her at the end of a nice, relaxing evening.
In the letter you can explain everything clearly without getting all emotional, and she can read it in her own time. The benefit is also that she has time to figure it out for herself. That way it wont put her on the spot. Sometimes a person's initial reaction might be harsh or negative, just because it is unexpected and come as a shock.

I know I would've preferred to find out in such a manner.
Good luck

Kaylyn,
To help you with your dilemma, I will quote my dear Dad whom passed away in 2006:

"Oh! what a tangled web we weave, When first we practice to deceive" - Dad & Sir Walter Scott, 1st Baronet.

Honesty is always the best policy.

Sounds to me that kaylynn is ready or at least wants to tell but is looking for advice on how to. Ok, honesty, sure of course. But that is not saying much other than the obvious. So what I will add is that it be done in person. Pick a time when you have plenty of it. Try as best you can to pick a time when stress is at its least. Start off by explaining that you feel close enough to her that she is important enough to you that you feel she should know. Then simply tell her you cross dress. She will likely have many questions. Answer them and be patient. Don't get upset at questions like are you gay or do you want a sex change. Those are always natural questions that come up. Don't be upset if you have to answer some of the questions more than once. Be patient. She may simply need time to digest this before a Conversation begins. I wish you the best.

i think you have to decide what you can live with and be prepared for a variety of responses...she probably isn't going to jump up and down and say "fun! lets go dress you up!"...in reality her response is probably going to be luke warm at best. I think it is important to discuss expectations and understand what you are willing to give up for this girl. But she also needs to be able to decide what she wants to put up with, that is only fair.