My first crossdressing purchase was a red wig during halloween.
But my first clothing purchase was about a year later. It was a longline bra at a lingerie store. I felt bad lying saying it was a for a girlfriend. And she told me girls my age wouldn't like it. I always wondered if she knew I was buying it for myself. I was planning on buying shoes and a dress or skirt that day but got too nervous after the first store. I haven't purchased anything since.
