October 19, 2009 3:26 AM BST
Hey Leigh!
I understand your position entirely; just at the beginning of this year, I owned nothing of my own, and just dealt with the overwhelming desire to dress as a woman by imagining myself in various items of clothing. My girlfriend, however, has encouraged me to new heights, and I now own two skirts, a pair of heels, a pair of tights and two blouses. It really helps to have someone physical to confide in, but this website should also be a great resource. I would recommend by seeing what sorts of outfits you like, and what you feel would compliment your figure the most. Also, I have always purchased my items at thrift stores, as most of what you see is the same as you would find in a department store. This gives you the fiscal ability to experiment without going out too far on a limb for anyone article of clothing.
I would love to hear more from you in the future! Stay in touch.
Stan
February 16, 2009 3:01 PM GMT
Hi Leigh, welcome to TW. As far as answering your question, you have to wear what you are comfotable with. I would recommend looking around the high street and see what other women are wearing and dress accordingly if you want to blend in. Your own personal taste will come into it of course but until you start experimenting with outfits and colours you don't always know what works for you. What looks good on someone else won't always look equally well on another person. You have to understand your body shape, size and spend some time figuring out what works for you.
Nikki