First time I ever crossdressed with my girlfriend

September 19, 2009 at 4:08 pm (Crossdress, Uncategorized) (, , )

This is such a fond memory for me.  It was about a year and a half ago. I had been with my girlfriend a few months but I had told her from the very beginning that I crossdressed. She didn’t really understand what that meant, or what it meant to me but she didn’t judge me either. She said she would try to understand and support me as best as she could.

This particular day we were in Dublin shopping and there were some other people with us. I found it difficult as she and the other girls were looking at girls clothes and buying and trying things on while I couldn’t even look or admit to being interested.

That evening I was very down and went to bed early. I was lying there reading when she came up and asked if I was ok etc. With enough prodding from her I eventually admitted to how these things make me feel. She said she had considered that during the day but didn’t know if she should bring it up.

She asked if I’d like her to put some makeup on me so we did. I was self conscious but it felt lovely. She did my makeup and it was better than anything I had done before. It felt great. Then she asked if I wanted to get dressed. I thought I’d pick some of my clothes but she thought I’d like to try some of hers for something different.

First I put on my own control panty (to keep things in place) and bra, and my fake breasts made out of tights filled with rice!

Then she took out her bag of tights and I tried on different ones. She had loads with different colours and patterns. We settled on a black very opaque pair with kind of diamonds pattern. I can’t remember the proper name for it. They were really tight fitting and felt great.

Then she got me this kind of long sequinned black lace material skirt and a black top to go with it. The top was cool and had a kind of thing you tie up around your neck and a kind of long sleeve cotton cardigan thing with it. It was a very elegant outfit. I felt fantastic to be sitting there with her wearing all her clothes, her tights and everything. I was wearing my own long black boots with a strap detail on the side, and a 2 in heel.

Felt so good to be encased in that stuff. We fixed my wig and took some pictures. I told her if she didn’t mind I’d really like to go out in public for a while as I hadn’t done it in quite some time. She agreed no problem and we got in the car and drove to a small town about 15 minutes away.  As I stepped outside the door of the house and felt my legs in the tights brushing against the material of the skirt it it was wonderful. I loved hearing my boots crunching against the gravel.

When We arrived in the town it was about midnight. I saw an oldish man walking home from the pub, in our direction. I got my girlfriend to let me out of the car and drive on and I would walk to meet her. I wanted to walk past the man in  these clothes. I got out of the car and felt the breeze through my skirt on my tights. I stood up and saw some girls in the distance. I wondered could they see me, and did they think I was a girl. The man walked past me and just smiled.

I met my girlfriend again and got in the car and drove further down the street. We parked and walked for a bit but I wanted to go back as my confidence wasn’t the best at this time. That’s the way it is I find. Sometimes you don’t mind and you can do anything and not care, while other times you#re afraid of everything.

Anyway, that’s pretty much the evening as it happened. It wasn’t the best from a going out crossdressing point of view but it is very special because of the fact that my girlfriend got involved and helped me. This will always mean a lot to me.


1 Comment

  1. Major Myths, questions, psychology and a how-to guide « Adventures in Gender said,

    […] article about the importance of telling her the truth. If you do, something like this might happen (blog post about the first time he dressed with his […]

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