This week has been awesome. I spent Sunday in San Francisco with Allie and Kim bumming around town and seeing the city, plus having a wonderful dinner. I've spent the rest of this week transforming into Jennifer almost the second I get home and hitting up stores and restaurants. Today I realized when I looked in the mirror I actually LIKE my makeup job, I look like I have real breasts, and I just feel comfortable in women's clothing.
It wasn't always this way, and I know there are lots of crossdressers on the forums that could learn from all the dumb mistakes I made. So, without further ado, here are the ten things I wish I knew when I first started crossdressing:
1. It doesn't go away. I tried so hard to quit. I purged multiple times. I dumped everything. I beat myself up about it. But the desire doesn't fade. You can fight it, but it'll just make you mad. I found it much more healthy to accept crossdressing and put limits on it. For me, my rules were home was off limits so that my family could always have Dad. Knowing when I could and couldn't crossdress gave my life a lot of balance.
2. If you're overweight, use crossdressing to slim down. I hated having to shop in the women's section. I would see a cute dress and realize it was a size 16...so close, yet so far away. I'd always struggled with my weight, but crossdressing finally got me to knuckle down and lose weight. I realized that while I regularly worked out, I ate a ton, and a lot of it was just social. I would eat whatever was put in front of me because it was there. So I started pushing food away. I also took gracinia cambogia to help cut my cravings. I asked my wife to make me smaller meals. I deliberately wouldn't take cash to work so that I would only eat my packed lunch and not buy snacks. All of that worked, and I went from 225 to 175. I used to be a size 20, but today I found I can now fit in a size 14.
3. When you shop, say it's for you. I struggled with this. I always used to lie and say "Oh, it's for my wife." Thinking back, I don't think one store associate ever believed me. I finally got the courage to go to a Lane Bryant and ask to try on clothes for myself...and the store associate darn near hugged me! I spent 100 dollars and walked off beaming! Most store don't care at all. Seriously. And most shoppers won't say anything, either out of fear or lack of care. Heck, after a while, you might get good enough they don't notice. Besides, if the store refuses to let you try on clothes, would you want to shop there anyway?
4. Keep a makeup journal. Especially if you're a part time crossdresser like me, keep a journal. Everytime you go to MAC or Macy's or wherever, take notes. Write down techniques, colors, whatever you need to remember how to do it. Heck, make it a scrap book and take photos. You'll be surprised what you forget.
5. Talk to people. I still suck at this, but seriously, talk to people. Ask the store associate how his day is going. Tell the mom standing next to you her baby is beautiful. If nothing else, simply pay someone a compliment. Nobody is going to scream "Oh my gosh you're a crossdresser!" if you pay them a compliment; in fact, they'll probably smile and you might just make their day.
6. Until you practice, plan out your time. I can now simply walk into my hotel room and in an hour become Jennifer, makeup and all. It was NOT that way for a while. Starting out, take your time. I tried to rush and I'd inevitably forget things, or look like crap and be self conscious, or not have a backup plan. It would make what should have been a fun evening very stressful. If you think you need an hour for makeup, give yourself more time so that you aren't rushed before dinner.
7. Don't forget the accessories. Crossdressing was all about skirts and dresses for me. After a while, I realized that if I wanted to pass out in town, I needed all the accessories: purse, scarf, jewelry, nails, lip balm and a sparkly headband. With these, I don't feel like a dude in a dress. Instead, I feel a lot more put together, and a lot less nervous. Don't forget pants too! I've fallen in love with yoga pants and girl jeans.
8. Talk to other crossdressers. This forum rocks for meeting people. You don't have to go out en femme. Some of the best dinners I've had are with fellow crossdressers while in guy mode. Just meet up for coffee, or lunch, or something small. You don't have to talk about crossdressing either (for most of us, it doesn't define us). It gets you out of the closet and helps you talk with others in your situation.
9. Do normal stuff. When I first started crossdressing, I met a girl that always wanted to go clubbing. It got old fast (and I was 25). Today I went to a quiet sushi restaurant and enjoyed the food in a nice top and maxi skirt, and I even caught the guy next to me checking out my cleavage. Dressing up for something like a club or a prom can be a blast, but often times it's the day to day stuff that I enjoy the most.
10. It goes as far as you want it to. There are always people who want to pressure you to do more, and there are others that will pressure you to do less. Ultimately, none of them are you. Don't ever feel like you are "just" a crossdresser. Nobody can make decisions for you on whether to get therapy, whether to tell your family, who to tell at work, or if you should take drugs, because frankly nobody else has to live your life. So decide where you want to go and go there, and don't fill other people's expectations.
And a bonus one...
11. Get a big sister. I consider John Warrener from tgfashions.com the closest thing I have to a big sister. I wish I was back in Massachusetts to be able to visit him again. If you can, find a big sister and meet up. Hang out. Do makeup together. Chat over coffee. Let that person help you. For all you know, you'll make a friend for life.
Originally Posted by MelanieAnne
So I think your #10 is the most important and only universal truth and should be top, front and centre... 
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