What should I do? any advice? (love to hear the opinion of both, sisters and gg's)

[naye]

Hi, Im kind of new in Toronto and since I moved to this city I decided to start accepting my cding side a little more and started buying more clothes, etc, and since I have been quuite lonely Imhavemt been afraid of being outed.

Since a couple of weeks ago I have dated a lady that I am starting to like a lot, an it seems thaat quiite soon we are going to go intimate for the 1st time. But since almost 1 year ago Ive been underdressing 24/7 and nowadays I dont have any male underware.

My question is what woukd you do? If youd go and buy male undies and stsrt using it in a regular way sonit wont be any issue when there comes the moment to be intimate, or youd just keepmunderdressing at usual and when that moment arrives just act normal and perhaps ask any possible quuestion and hope for a good reaction, or give her the "warning" before thst happens and see how receive the news?

I know that honesty is always the best thing, but I dont know if its to soon to let her know, and sometimes I think thay perhaps to tell her in advance it could be like accepting thst there is something wrong with thst and thsts why I giving her an explanation in advance.

What I woukd love to do is to act normal and when that days arrives just act as it is, just a piece of fabric, no big deal and see if she could take it that way, or should I just stop underdressing until we advance a little further in our relation?, Id appreciate any advice from any of the sisters and it woukd be nice to know the opinion of any GG. THANKS!!!!

[PaulaQ]

I would not surprise her at an intimate moment with this. Before the night you are going to be intimate, I would tell her that you really like her, you feel like you totally trust her, and that you'd like to share something about yourself that you've shared with NO OTHER person. NOBODY!

And then tell her you are a cross dresser. Just tell her the truth. Don't be ashamed of it - there isn't anything to be ashamed of. You didn't ask for this, it's a part of you as surely as the color of your eyes, and like your eye color, you were born this way, as best we can tell.

I think surprising her with it is a bad idea because it isn't just clothes - and we all know that's the case. There's something else about this, and it's important to us, often for reasons we can't even articulate. It is also only fair to tell her because like it or not, society still thinks a man who crossdresses is at best pretty unusual.

I think your best chance is to tell her as sincerely, and honestly as you can. Show her you can be vulnerable. Yeah, this is a risk, but if she isn't going to accept it, she just isn't, and it's definitely better to do it now than to wait until you've been married 10 years...

She may well surprise you positively, though. I think sincerity and honesty are your best tools. Don't come off as if you are apologizing for it. It's OK to tell her you've always been ashamed of this, or afraid to talk to others about it.

I hope it pays off for you, whatever you decide to do.

[naye]

Thank you very much for your words Paulam Ive been quite nervous about this and honestly the only reason why we havent made love yet is because I try to evade her when we are alone because I know what is under my pants :$. Im quite stressed about this.

[Rachelakld]

I don't think dropping down to womens undies is going to excite her, probably the opposite.

For me, my special night 7 years ago, I made a lovely meal, soft music, wine.
At the end of dessert, I mentioned how much I enjoy womens clothes and asked if she would like a look at my wardrobe.
After 30 minutes of us both playing dressup and her admiring my taste in clothes, we both found ourselves without clothes

Everyone is different, and if she wants to run, better now while you both have the rest of your lives, than trying to re-start your lives at 40 or 50 etc.
Most GG are upset more by living inside a lie for decades, than the actual cross dressing.

[MatildaJ.]

it seems that quite soon we are going to go intimate for the 1st time.

honestly the only reason why we havent made love yet is because I try to evade her when we are alone because I know what is under my pants.

If you have been evading her sexual advances, then she is probably worried you are gay. I think Paula's right, that you should explain yourself to her before trying to have sex. But if you're nervous that she is going to be judgmental, you can start by talking about crossdressers in the news or about a crossdressing friend of yours, to see how she reacts when it's not quite personal.

[PaulaQ]

Hey, one thing I would also advise you - DO NOT - use the term "transgender" to describe yourself. In many people's minds, especially thanks to the usage of the term in the news as related to transsexuals, "transgender" is a synonym for "transsexual". You don't want her to think this unless you are certain this is what you are. You seem quite far from that - so I think just the term "cross dresser" is probably for the best.

We have endless debates about the word "transgender" on this forum, but my opinion is that for your purposes, there's a risk that term carries too much baggage.

Lookit - I'm transsexual - and *I* often describe myself as "transgendered". It technically speaking actually could apply to you - you don't have to change your sex to be transgendered. But you don't want to explain stuff other than things that pertain directly to you, and what you actually do.

[Gardener]

Most GG are upset more by living inside a lie for decades, than the actual cross dressing.

Very true.

I think I would separate out these emotional and significant events as much as possible. It might all go well but overload is a big risk. Perhaps this is easy to say than it is to feel but it sounded like naye was also a little bit embarrassed about an aspect of herself?

[Beverley Sims]

I would get male underwear and if the situation develops into something serious, then you need to tell her before you get too deep into the relationship.

[naye]

Thank you for all your responses, Im thinking in going to buy some male underwear at least for the first couple of times before opening to her, perhaaps Im a coward but I dont know if Im already prepared to tell her

[Melissa in SE Tn]

I don't have an answer, but would love to hear how it all played out.

[sandra-leigh]

I recommend telling her before the first time. You might still have some male underwear on hand in case she asks you to put it on "while she gets used to the idea". But for whatever reason, people tend to feel lied to and violated if they are not told in advance before the first physical intimacy.

[Kate's at home]

Wonderful suggestions Paula! Honesty, openness and vulnerability...it will show you care about her as you also are more fully yourself with her in the process. It's another step... I went through this several years ago. I know how scary it can be, and continue to be. We are now married and, periodically, we have to revisit the boundaries of what is "OK" mutually, in practice and intent (this is where Paula comments on CD vs TG vs TS become so incredibily important).

Best of luck!

Kate