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We called it, "Liquid courage", Claire. At your age u may feel u need it to express yourself. I was the same back then. Drinking and partying was a lot of fun but it got me into a bit of trouble. I never picked fites with guys that could easly injure me unless I was drunk. I outgrew it. While I used to drink moderately when I began dressing 17 years ago, I find it a distraction and a buzz kill from the natural high I get from dressing now. If u keep drinking like that? U may need professional help eventually.
Tell your GF only if u have to. Or, if u r getting bored with your relationship? That could either refresh or finish off your affair with her.
Very few folks r like Abby above. Who married at 26 and still r together 16+ years later. Start looking for a life partner when u know who u r and a success in your chosen field. You'll have a much better statistical chance of being together for 10+ years then.
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I can definitely sympathize with what you were saying. I purged when I thought I could will it away and just be a normal guy. Purging is a terrible idea (unless you like to rebuild you collection of femme stuff) and I've seen suggestions from people on this forum that if you get an urge to purge, stuff everything in a box and stow it somewhere you feel is safe. That way, you don't waste anything and you can bring it back when you feel it's appropriate. After purging, I started getting back into dating and a few months later, I met my now fiancé. Being in a relationship in the beginning made it easy to forget that I even cross dressed but later on, I started to get the urges again. I thought I could resist it (as you know, that may not be possible for everyone) but I found myself looking at women's clothes again and longing to have that feeling of dressing up. I soon realized that crossdressing was a part of who I was and if anything were going to progress with my relationship, I was going to have to be open and honest with my girlfriend. I told my girlfriend and she was as supportive as I could have hoped. She was shocked of course but after I had explained to her about my personal situation, she was sympathetic. I only tell you this because I didn't realize how much of a weight had been lifted from me when I came clean. The result of coming clean often doesn't turn out positive but it all depends on the situation. That being said, no one can or should tell you how you should live your life.
As for going out, I've only just recently starting going out in public. From what I can tell you based on my experience (especially from a very conservative area of the country), it has been a positive experience. There's plenty of people on here that have had the opposite experience but if you plan out your trip well and use common sense it can be worth the risk. Once I finally went out on my own, it was the most thrilling and fun I had. Crossdressing can be fun at home but to put in all that work on getting your look just right, sometimes you just want to show it off. I hope this helps, I was in you shoes (women's size 11W, har har :P) not too long ago so I thought I'd share my experience.