Most of my shopping I do in “drab” mode. My wife and I like to spend time together browsing the second-hand stores or the clearance areas of department stores. She likes that she doesn’t feel rushed since I don’t get bored and impatient like most husbands. She doesn’t mind that I will look for women’s clothes for myself even though she prefers not to see me dressed in them. Second-hand stores are great because you can get a lot of items for a little money, don’t get harassed by sales staff, and have changing rooms that are usually not strictly attended. Of course the down side is that you rarely get newer styles and the items may be imperfect. I've bought a few things over the internet at sites like Glamour Boutique but prefer to buy things in person.
Many cross-dressers have no compunction about shopping anywhere no matter if people are aware they are shopping for themselves or not. But I think I am like most CD’s in that it still makes me a little nervous. From October through early February there is the built in excuse of the holidays (Halloween costume, Christmas present, Valentine’s present) that make shopping for women’s things a little easier. It’s funny; it doesn’t matter what time of year it is, if I’m actually shopping for something for my wife, I am quite comfortable shopping for any women’s articles but if I’m shopping for the same thing for myself I feel like everyone knows exactly what I’m doing.
Depending on how I’m feeling I will usually just buy things without trying them on but if I need to I will take women’s clothing into the men’s dressing rooms. I even did that with wedding dresses a few times. I did a blog post about that.
If I’m feeling a little nervous I might grab a suit jacket and drape that over a feminine item that I’m bringing into the men’s dressing room.
A few times I have shopped enfemm. I take the advice of most CD’s that have done it and have dressed down since that’s what most GG’s do when shopping. I’ve not had any problem going into the ladies dressing rooms and was even directed to the ladies dressing room when I approached a men’s dressing room that was not clearly marked. I find if you just act like it is perfectly normal and are polite to everyone then the probability of an incident is limited.
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