So...I finally told my GF.
I have recently become quite happily reacquainted with a woman from my past, we have dated twice before, the first time being almost 18 years ago when we were both very young. Back then, when we were playing in the bedroom she would frequently ask me to put on her dresses, etc. I could see in her eyes that this was something that she would very much like.
I have been CD'ing, to some extent, since I was a child. In my high-school years I was caught once by my aunt, who I was living with at the time, and was made to feel very ashamed about it. I am sure that this didn't help, although I am not making excuses here.
I only let my GF put a dress on me one time back then, because I knew it was something that she very much wanted, but at the same time I was very scared of her finding out my secret. I thought that she might see that I was enjoying it, etc. At that age, I was terrified of anyone finding out, I still am now too, I suppose.
I have often thought about those times over the years, usually with regret. We dated a 2nd time about 6 years ago and I considered telling her but again was horrified at the thought of her reacting negatively. We have been seeing each other again for the past few months, and it has been phenomenal. She takes such good care of me, despite living 5 hours from here. I am positive that this is the woman I want, need to marry.
While considering the marraige question, crossdressing naturally came to mind as well. I finally decided I have to tell her, so one night over the phone I told her that I had something important to tell her but did not want to do it over the phone, as I was uncomfortable and wanted to do it face to face. She came up to visit the following weekend and asked me what it was a few times and a managed to change the subject each time. (Chicken!)It was sunday afternoon and she was to be leaving soon... I decided now is the time.
"Do you remember how you used to always try to get me to try on your clothes?" Of course she said yes. "Well... I've been wearing women's clothes and lingerie in private most of my life..." Her face just lit up. "Really?!" Followed by, "Oh baby, why didn't you ever tell me?!" I told her it was because I was terrified!
That was a couple of weeks ago, and we have been talking on the phone/skype a lot since then and she has been just unbelievably amazing about it! I told her so late in her last visit there was no time to discuss it much further. I believe now that this was a subconsciously done on purpose in case it didn't go as well as I had hoped. Anyway, to make a long story even longer, I would never have dreamed that she would react the way she has. She is incredibly excited over this, and has been gathering all kinds of stuff to bring over next weekend, wants to dress me, do my makeup, bought me a new wig today, I just can't believe my luck! We are having a dinner date at my place, where she has told me that she plans to fix me up and seduce me.
I truly understand the crippling fear we all have faced, or are facing, with regards to this dilemma. Based on past history I had a feeling that telling her would be a positive thing and I was still too terrified to tell her for 18 years!? I suppose the moral of the story is, you never know, and if you have the slightest idea that your SO may be into it, it is definitely something to strongly consider. I'm no longer sure where I am going with all of this, and apologize for the length of the post; but I finally had to say something because I AM SO EXCITED! She is the most amazing woman, and I have truly struck pure gold with her, she has made me so happy and I just had to share! I am sure there are lots of things I am leaving out but this post is long enough already..
Thanks for listening!
Lisia
