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Shopping as a Crossdresser

crossdressed in the Kohls dressing roomThe only thing better than shopping for women's clothing is doing it while dressed up as a woman. Probably half of my wardrobe was purchased online or me out and about as a man and coming across something that I just had to have, but the other half was purchased while on shopping sprees dressed as a woman. There isn't a bigger thrill than going out in public, scooping up an armload of clothing, and heading to the dressing room to try everything on in front of those full-length mirrors. Of course a lot of the thrill is also wondering if anyone is on to you. Sometimes I get nervous if I suspect that someone is watching me extra close, but at other times I simply don't care. I guess it depends on my mood that day (see my entry on that Gap dress for an example), but ultimately I have to remind myself that if someone suspects that I'm a man in drag, it's because I am a man in drag so who cares?

 When I dress up for an afternoon of shopping, I try and keep it quite conservative so as to not stand out. I'd love to wear a tight top, short skirt, nylons and high heels, but how many other women do you see dressed like that to shop? As a result, I'll usually wear my denim capris with a long sleeved top (like the picture at right) and strappy sandals with flat heels.  Occasionally I will wear a blouse, skirt, nylons, and heels when I shop, but I try and limit that to times when itd be normal for a working woman dressed up to run into a store for a few minutes. One of these days I also plan to take an old ID badge from work and superimpose a picture of me as a woman over the top to further enhance the working woman get-up.

I have never gone to a shopping mall while dressed up due to the fear of all the people there and thinking that someone will surely notice. For some reason, I have this fear that teenage girls or girls in their twenties that comprise the staff at clothing stores would be more perceptive than older women or men, so I try to avoid places with a female sales staff that actually approaches the customers to see if they need any help like in a shopping mall. 
shopping crossdressed at Target
It's funny because on one hand, I want to melt into the crowd and go unnoticed, but on the other hand, I want people to notice me and think to themselves that I'm actually a woman and a pretty one at that. When I go out to shop, I usually stick to box stores like Walmart (not to buy clothes!) or Target, or I also like to go to thrift stores. I have to be reasonable and understand that spending $40 for a cute top doesn't make much sense if I only get to wear it once a year, so I love to frequent second-hand stores or thrift stores to buy most of my clothing. Sometimes you come across some really nice brand-name clothing in the process.

When I shop for groceries while dressed as a woman, I must admit that I will always choose a store that has the self-serve registers although sometimes they will be closed, and I'll have no choice but to go through the normal lines. It's times like those when you perk up, stick your chest out, and be as polite as possible. I try to maintain good eye contact, smile, and of course say very little.
crossdresser shopping outfit
If my family is out of town visiting my wife's family, I'll spend the week dressed as a woman as much as possible. I even set the rule that if I go out to shop or go out to eat, I have to do it as a woman. It just adds to the adventure of dressing like a woman in public.

 As for the contents of my purse when I go out dressed, I always take a hair brush, a small mirror, a tube of lipstick, my drivers license, and plenty of cash. My wife has enough wallets and purses as it is, so I just borrow those from her. No use spending good money on those sorts of things with all those clothes to buy.

As for my outfit pictured at right, it's a Banana Republic cotton blouse that is tapered nicely at the waist. It is also white and see through enough that I have to make sure I've chosen the right bra to wear. The denim capris have the name brand of Arizona, and they are size 14 1/2 which makes me suspect that they are actually girls capris as my normal size when shopping for jeans at Old Navy for example is 8. I purchased the sandals at Walmart and still remember I was dressed in this outfit. I'm wearing Leggs suntan pantyhose underneath. Often I will wear Leggs toeless pantyhose in a nude color, but for this picture I had on suntan pantyhose with a sheer toe. Click here to see a few more poses of me in this outfit. 

Cocktail Dress


Skirt from Polo

Ann Taylor Again

Ann Taylor Outlet

Kohl's Intimates

Polo Outlet

Elle Dress

Fun at Ross

Old Navy Fun

VF Full Slip

Black Friday

New cargo pants

Sandals and Skirts

Summer Separates

Shirt Dress

Black Bra Tops

New Year, Old Navy

Black Bra N Panties

J-Lo Sweater

White Shorts

Femme Hygiene

Summer Wedges

Daisy Dukes

Flats at Target

Hardware store and In-N-Out

Old Navy for July 4th

Walgreen's and Ross

Spring Tops


New Earrings

Outlet Shopping

Christmas Panties

Boot Shopping

Skinny Jeans

Christmas shopping

Dangly earrings

New Tights

New Makeup

Bra at Kohl's

Old-fashioned Bra

The Perfect Denim Skirt

Yoga Mom at Wal-Mart


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