I let the cat out of the bag....

Well today I went and did it! I told the lady I've been seeing of my desires to become a Crossdresser. And after the "Shock and Aww" wore off. And my reassurance that I'm not Gay, BiSexual maybe. I think she really started to understand my fantasy and desires. A few weeks ago I had decided to tell her when the time was right. That choice was based on two things, first the freedom to be honest about my thoughts and two to give her the choice to be accept and be apart of it or not accept it and move on. Either way it would be a win/win for me. So she decided to be apart of it. She even stated we should dress up for Halloween, She as a boy and me as a girl. I'm not to keen on that but maybe. She said we could go out partying to clubs and bars together. She also stated she will help me with the makeup. So my question is this...After all is said and done will this work out? Has this happened to any of you? And where did it lead to?

ps... She also stated if I wanted a sexual relationship with a man she want to be there to help protect me... Good Idea or Not?

Wow. Just wow. Sounds like the kind of fantasy a lot of us here have. Nothing of the kind ever happened to me, but I think I would have liked it. There's no easy answer to the question in your mind: how is this going to work out if you follow the inclinations that both you and the woman seem to be having? Everything depends on things that you can't know for sure. So it's a risk either way: to not go with it might mean you've missed a great opportunity; to go with it might take you to some crazy place. Like with so many other things in life, you just have to make your choice and hope for the best. Not that you should make your decision based on what anybody else says you should do ... but ... I say, go for it, girlfriend!

First, congratulations on a job well done. Second, relations all vary and all have their discovery period, the courting ;period where most of us put up with a few things that sometimes bother us. In your case, you just added one more issue, which can be a very big issue depending on how both of you handle it. Since you are being honest up front and felt comfortable enough to reveal it to her, you may have a very good chance to make it work in the long run. What is needed in any enduring relationship is very good communication, even if it means getting to an "agree to disagree" point over certain issues. The ability to communicate well, openly and honestly, and sometimes even more importantly, diplomatically, also depends on the overall communication process, which includes tone of voice, timing of serious conversations, ability to listen without prejudging and over reacting, the use of safe words like ":Let's talk about this later after we think a bit more about it.", and many other techniques and little tricks of the trade that you will develop over time. I wish you the best of luck.

From experience I doubt this will go the distance..so enjoy it it while you can

first, yes, its a good idea to get out and explore with her...the partying, clubs and makeup assistance all sound like fine. This is what you asked for, so go with it and see where it leads.

As for the sexual experience with me, why as us. If you are interested in that sort of thing, then, fine, take her up on it. If its not your cup of tea, tell her so.

Yes don't miss out on this, it is a chance of a lifetime!!

Iris,

That's a loaded question: "Will it work out?" I agree with the previous post about appropriate communication. I would also point out that sexuality and presentation are only part of a relationship... Do you enjoy other activities together? Do you make each other laugh? Do you share political views (i.e., what else might you end up arguing about)?

Good luck!
Lee

I'd run with it and take it as far as I could.
Sounds like a great opportunity to explore yourself even more.

No one can tell you if it's going to work out, you just need to keep working at a relationship, that's all there is to it. I don't get the part about her protecting you? Is she stronger than you or something? :P

Forget the last paragraph.
Go with her for Halloween in the way she suggests otherwise you are showing a bit of hypocrisy here.
Go slowly and only move on her suggestion, that is the best way.

I’m pretty sure that a lot of first went out on Halloween. In your case it sounds like a fairly safe outing, after all, your girlfriend is crossdressing as a boy while you cross dress as a girl. When asked who did your makeup you simply explain that your girlfriend did your makeup and helped you with your costume. I’d go for it. Who knows this just might open up a whole new world for you and having a supportive SO is one huge bonus.

I don’t think it is all that uncommon to wonder what it would be like to have sexual relations with someone of your own sex; I think it is a lot more common than most people think. It might turn out that it is something that you want to continue doing, on the other hand it may convince you that once is enough and you definitely prefer sex with a woman. I strongly suggest that you take precautions to ensure that it is a “safe sex” encounter and in a safe environment.

As for your girlfriend being there, I think you will quickly find that she may have more on her mind than your safety and that the three of you are engaged in a ménage Ã* trois. Now that is something that many dream about and few ever get to experience.

Iris,
She seems to have reached out to you after your admission. Take it as a genuinely honest gesture and accept her suggestion. She seems to really want to have a relationship with you and one that integrates your cross dressing. I believe that this lady is very accepting, so accept her in return. It will be a very interesting journey and one that will allow you to fully explore your own sexuality. I wish you both every success.

Iris,

That is amazing. That is a story of acceptance most of us could only dream of. Go slow and enjoy. Maybe it will work out, maybe not and maybe she is one of the open minded GGs in the world. I do pray it all works out for you!

Hugs,