When I was eighteen, I built up enough courage to go out and buy some clothes. I went to a supermarket and bought some tights, and went home and put them on. I loved the feel of them and the thought that they were my own really thrilled me. Not long after I went to some charity shops and bought a pair of high heels and a dress (neither of which fit me properly).
A couple of weeks later (after an incident where I was almost discovered) my courage ran out and I threw my stuff out. A few months later, I was desperate to dress again, but I didn't want to wear my mother's clothes again. There was a young woman at work whom I liked. I was sexually attracted to her and I really admired the way she looked in her clothes.
A couple of times I would drop hints, in a joking way, about dressing as a woman but, she never thought anything of it. Finally after one of these jokes I said to her, "I do like to dress as a woman." It took me a while to convince her it was true (I finally convinced her by wearing a pair of tights under my trousers.) She was supportive and helped me to feel less guilty about what I did.
She gave me advice on clothes and makeup, and I began to gradually get my courage back again. After another couple of months I told another girl, and she was great at first and we went shopping together. However, things started to fall apart when I wanted her to come and see me when I was dressed. She didn't want to, and this put a strain on our relationship. Not long after, we argued about something else and I haven't seen her since. I am sure that my cross-dressing, though it wasn't the main cause, was a factor to our falling out.
Despite this, my courage had grown and I started buying more clothes. I only dressed in private, and still hadn't the courage to go out. Then, about two years ago I met my current girlfriend and I told her quite soon in our relationship as I felt it wasn't fair to lie to her. She is absolutely fantastic and helps me with shopping and makeup, and doesn't mind me dressing up when she is around. She does get worried sometimes and I have to be careful and be sensitive to her feelings. All in all she is nothing but supportive.
I now have much more courage, and I go to a support group regularly. I've been out to a bar twice, but am afraid of being seen by someone I know. I don't want to come out because I feel that my family would be too shocked and it would ruin the excellent relationship I have with them
I went out during the day for the first time about four months ago. I took a day off work, hired a car, and drove to a far away city for a day of shopping. I spent the whole day going round the shops and it felt fantastic. I got read a few times but most people either didn't notice or just didn't care. I stayed dressed until I was about 20 mins from the house. I couldn't bear the thought of going back to my old self again.
I don't think I am TS, I like to be able to become my female self when I feel like it, then change back when I don't. I don't think I would enjoy being a girl full time. I still have some pangs of guilt but gradually I am coming to accept, there is nothing wrong with what I do so.