The Perils of Shopping

Boy, have I had some narrow escapes while shopping for my ‘special’ wardrobe!

Shopping is one of the greatest pleasures for a crossdresser; but can be fraught with difficulty. You can feel like a child in a sweetshop one minute and then like a fugitive on the run the next. Let me give you two scenarios. 

In the first, Scenario One, you are on a business trip, far from home. You have some free time and have found a charming little charity shop just around the corner from your hotel. You go in. The shop is deserted apart from a lady at the counter who gives you a lovely smile of welcome. When she notices that you are browsing in the Ladies’ section she points out that there is a changing room at the back and says that if you need any help you should just ask. She comes over to you and comments that the dress you are looking at is gorgeous and would look lovely on you. She asks if you are looking for anything in particular and helps you browse along the rail giving a little commentary of what she thinks would suit you. You soon have an armful of beautiful dresses and she leads you off to the changing room. You are in Seventh Heaven. The assistant – her name is Margot – seems as at ease with your dressing habits as you are. She knows exactly what you want and you have just decided that you are going to resign and move to this city just because of this shop when the doorbell goes and in walks Scenario Two. 

Oh my god! It is your boss. Of all the people in the whole world he is the worst possible person to appear. You have a promotion interview with him on the following Monday, he has never liked you, and he is friends on Facebook with absolutely everybody you know. A yawning hole appears in the pit of your stomach and you break out in a cold sweat. You look down at the mountain of dresses you are carrying and then pleadingly at the face of Margot. But she has changed. She is not the same warm, friendly Margot. She is now looking most disapproving. You are caught in a pincer movement. There is no escape. I won’t take up your time with the horrible details that are too painful for you and I to imagine. Suffice it to say that you do end up moving… to a completely different City. You do get a new job… in the sewer maintenance department. And all your family and friends? Well you don’t need to worry about them… ever again!

Now, ok, I have picked two extreme examples, for illustrative purposes, you understand. The above horror story is highly unlikely to ever happen. And if it ever did, you would just have to console yourself that you could just as easily  have been struck down by a bus or by a falling block of ice, or by some other cause that had absolutely nothing to do with ladies’ clothes. But the sense of risk and fear that this story stirs up is very real and is with us all the time when we are shopping. I myself have had some narrow escapes. I have been browsing in a charity shop when a family friend walked in. Thank the Lord I was not holding any clothing, and I don’t think she noticed what I was doing. But the shop assistant knew, and I have no idea, to this day, whether once I had made a rapid exit she had spilt the beans to my friend. On another occasion I was actually standing holding a lovely white pleated skirt dress outside the fitting room, waiting for it to become free, when I noticed a male work colleague browsing a bookshelf nearby. I was mortified. I slowly edged behind a column, hung the dress back up and and slipped out of the shop, staring furiously at the carpet. I once went to buy a pair of panties in a local store only to see one of my wife’s colleagues at the entrance. Thankfully, I had not committed myself and sailed straight on past. Imagine if she had met me in the lingerie section! ‘Browsing for panties? Who, me? No I’m carrying out a study of the properties of elastic, its very interesting. The report will be a present for my wife so please dont tell her!’ 

So how coukd I cope with this lurking anxiety that stalks us while we shop? I could stay at home and buy everything online. It might require setting up a separate bank account and renting out a confidential mailbox but there would be hundreds of thousands of items available to me. I could see them all before I bought, I could choose sizes that actually fitted, and mix and match to my heart’s content. But what a joyless experience that would be. The process might have become highly efficient, convenient and risk-free but any sense of experience, of exploration or experimentation would have gone. On the other hand, there might be a cross-dresser’s shopping Nirvana out there somewhere. A sanctuary-shop where the staff know me well, love to help me out and are the very paragon of discretion and confidentiality. 

But the reality is that we must live in the real world and to do so we must survive on our wits. We must use tricks of the trade that any private detective will be familiar with. We notice who is in a shop before we enter, or loiter outside until any male customers have left. We judge the likely reaction of shop assistants to our ‘uncoventional’ choices before we go to pay. We apply the art of camouflage by taking items of men’s clothing into the changing room along with our skirts and of distraction even buying several pairs of men’s briefs to sneak in a pair of lacy panties. Yes, there are great lengths we have to go to but these are the things that keep us sharp-witted. They stop us getting lazy. Keep us safe. These key skills are useful. They could be useful to others too, perhaps to our wider community. Wouldn’t it be great if we could offer our skills and services openly to the benefit of others? Perhaps I should start a business, place an ad in the Classifieds Section of our local paper. ‘Lilly Barton: private detective and cross-dresser’. I could help out people who have been let down by Justice and the Law. I would always waive my fee though I might accept donations of second-hand ladies clothing to add to the one or two items that I might buy while undercover. Wouldn’t it be just  great if, when some poor old lady fell victim to dognappers or a single mother was at her wits’ end trying to keep track of her wayward daughter, they could know that help is at hand and that all they need to do is seek out the services of a good transvestite!

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