Out Shopping

I’m not real crazy about shopping but do a fair amount of it to get new outfits for taking pictures and going out. For more fetish-ey kinds of things I often just buy online, which has its own hassles with returning things that don’t fit, but I also go shopping locally at places like Ross, Macy’s, Burlington Coat Factory and even Target occasionally. And like I’ve mentioned before, even after all these years, I’ll sometimes get insecure about being a guy looking at women’s clothes. I was talking to another CD the other day who said the same thing. He was planning to go out shopping in guy mode, made it into the store, and then lost his nerve and turned around and just kept walking. I’m sure many of us could relate, as it is often considered a bit odd, or at least unusual, to see a man browsing in the women’s department, whereas the reverse is no big deal at all.

To be honest, I’ve done it so much that I usually do pretty well but if I feel at all nervous it’s usually worse in the first ten minutes. Once I find an item that’s a possibility that usually relaxes me and I just focus on the hunt and get into it. Or if there’s a good song on the Muzak – I heard Macy Gray this afternoon – that can often put me at ease. But starting out can sometimes be slightly uncomfortable, especially since I’m sort of a nervous type to begin with. I know a few other CDs who have this relaxed confidence about them and who never seem to get rattled – yeah, that’s never been me. I’ve also known one or two who have an almost defiant quality to going out, and that’s something I also hope to avoid as it just comes off as angry and as if they have a chip on their shoulder (which, well, they seem to).

Of course, like so many things in life, it’s all a mental game. Most people really don’t care and if they notice or wonder about me at all it’s probably just a passing thought about the tall guy with shaggy hair over there looking at dresses. Then there’s also the whole question of going out shopping while dressed, which is something that I’ve never really enjoyed that much, as I feel like it draws even more attention to me than if I’m just some dude, and ironically enough, for someone who has lots of bondage pictures of themselves online, I don’t really enjoy being a center of attention when I’m out and about. I know other CDs who swear by shopping while dressed and say that’s definitely the way to go. In fact there’s a local CD and her wife who have suggested I should go with them, so I might try it again at some point.

So again, the real challenge is just in that space between my ears. Maybe I just need a nice prescription for some Xanax.

7 thoughts on “Out Shopping”

  1. Ya i know how you feel. I have some open minded girl pals and i pay them to buy me little things here and there. Mostly because when im in the womans section of any store i feel like im violating some sanctity or something. Even though its clothing. Its hard for me as someone who crossdresses(i have a lockbox full of stuff,until i get my own place)
    Ive always come off as a bit of a creep to most females (i dont know why,im innocent!) so i could never imagine myself going into stores. Its just self esteem really.

  2. I have gone out shopping dressed a couple times…and yes the attention is a bit nerve-racking…good or bad…luckily i havent had any bad, or i was just too in tune with what i was doing to notice. Yet, I shop mostly as a guy…and if it has been a while since the last trip, yes, the 1st 10 minutes is the hardest part. But normally i have something specific in mind, and once again…i just tune out, until i see an attractive woman…lol! But even then…they are the best to get advice and opinions from…maybe even a phone number. Its all about where yer mind is, and not worrying about everyone else…just be yourself and go about your business.

  3. Hi Sandra, Another great topic, and not an easy one. I have mostly shopped online or through catalogs over the years. There is a cost/hassle factor when things don’t fit, but I’ve had pretty good luck. I made a quick trip to a large Goodwill store last year and arrived when they first opened (not too crowded). The only issue was that the racks were so full – really hard search through. It was nice to be able to try a few things on before buying (I was looking at sweaters/tops). You can’t beat the prices.

    I’ve often wondered whether any large city thrift stores could be approached to have special events or designated hours for TGs. I would also note that some of the lower-priced online stores have really great options, especially JC Penney and Payless. I just got some super turtlenecks and sweaters from JC Penney online.

  4. I love the way you write: it’s deep, sensitive and very observant.

    Any person who gets to share any type of intimacy with you is very lucky.

    I hope to meet you in Denver or L.A. some day.

    You are very powerful, but you are very gentle with your power.

  5. I’ve done both in the past. It depends on what I’m getting. Usually, if I just need make-up or pantyhose, I’ll go up the aisle where the pantyhose are, with my little list in my hand, pick them up and put them in the shopping cart.

    The next time, I’ll have mascara, or eye-shadow, lip-color, something like that on my list. I’ll go through the toiletries, the sort of make my way over the make-up. Once again, with my little list out, like I’m checking it off, I’ll select whatever makeups and put them in.

    One day, I picked up some mascara from the discount table. When I got ready to do the self-checkout, it wouldn’t come up, so the girl helped me by ringing it up by hand. She looked at the price and said, “why can’t I ever find it at this price, and you guys always manage to find it?” Hmmmmmmmmm.

    I’ve also done my shopping while dressed. Then I don’t mind at all going in in wig, makeup, high-heels and hose and just loading up on pantyhose and makeup all in one trip. I don’t even worry about going through the hardware aisle or automotive first!

    But usually, my mode is to find something, just one thing, while I’m doing my regular shopping, and throwing it into the cart.

  6. There was a place I’d stop in at night sometimes and buy a cheap cappuccino. I’d usually talk to the clerk, a woman. One day I went in in the middle of the day, in guy mode, and bought something. I was surprised to see her on duty. So as she was ringing me up, she looked over her glasses at me and smiled and said, “How are you, Sir?”

    I wondered if she knew. So I waited until no one else could hear and asked if her she recognized me. She said, “I think so”. I said, “Last time I was here, I was about 5 inches taller”. She grinned and said, “I was just watching you, and I thought you might be her.”

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