I was in Kohl’s today returning Christmas presents that were the wrong size.  Did you know that Kohl’s has an Amazon return drop off?  I thought that was pretty interesting.  Part of my receipt was a 25% off coupon for anything in the store today. Well, a girl can’t pass that up, can she?  I came, I saw, I shopped.

My first stop was the intimates, all the pretty bras. I used to only look at the things that were displayed on the main aisle. I’d stand across the aisle and try to spot one in my size. I thought I’d look like a bored husband waiting for his wife.  I couldn’t actually venture into the ladies’ unmentionable section, could I?  If I saw a garment in my size I would jump across the aisle and grab it, stuff it under the man’s sweatshirt I was carrying and slink to the checkout. Only after I returned home would I realize that I didn’t like it.

I pried myself out of intimates and into the shoe section. Ahhhh shoes, I love shoes.  I have grown into being able to browse the section, looking for my size. Well, all the Kohl’s shoes stop at size 10. I need an 11, 12 is better. I see a pair on the discount rack that’s an 11. I pick them up and head for the bench to try them on when I notice that they are hideous!  Once upon a time I would have bought them, taken them home and worn them. Why, because they were my size that’s why. Not anymore, I hated them, put ‘em down and walked away.

Exceptional Voice

Next, I spot the big and tall section. Before I get there though, I bump into a former colleague, not a close friend but we have hung out before. We talk some, shake hands and part ways. Previously I would have just high tailed it out of the store in shame. Not anymore, I continue into the big and tall section. I look around a bit, run into him again but continue shopping. I find the sale rack, 50% to 75% off, I start leafing through the clothes when another woman joins me. I find the pinkest sweater I’ve ever seen, pull it out, it’s my size, I hold it up against me, I think will fit!  That’s when I notice my colleague, in the men’s section glancing my way. There was a time I would have died, now, I waved. On my way to the cashier I spot a stretchy cami top that’s cute.  I rummage around until I find one in my size and pull it out. The other women in the section take no notice of me.

The cashier and I make small talk as she rings my purchases up.  I used to have some sort of manly thing to act as “cover” and pretend to look for my wife. Not anymore as I pay the young lady, take my purchases and head home.

Oh, I didn’t use my coupon. I paid $13, saving almost $40.

Both the sweater and the cami fit fine.

I used to buy things that I didn’t like, didn’t fit and never wore.  I was petrified the entire time I was in the store. Today I enjoyed shopping like any other woman. I’ve learned that most people are too busy to care what other people are buying.  “He’s a crossdresser” is not the first thing people think when they see me shopping.

Today I noticed the change.  I’m no longer the scared little rabbit trying too hard to not be noticed. I’ve relaxed and by relaxing I blend in better. Blending in better allows me to enjoy my shopping more. Enjoying shopping will lead to more shopping.  I like that.

Bottom line is the fact that my shopping for feminine items has evolved over the years to the point where I feel comfortable at the stores in the ladies departments now. I don’t worry about what other people are thinking while I’m shopping for femme items for myself. I feel happy and comfortable in my own skin now while out shopping. This is how my shopping ways for my own female clothing items has evolved over the years!

  • How about you girls out there in Crossdresser Heaven land? Have your shopping ways evolved, similar to mine over the years?
  • Have you had any uncomfortable situations occur when out shopping for your own feminine items while dressed as a man?
  • Have you reached a level of comfort where you would take your feminine clothing items to a dressing room with a store associate out in the front of the dressing room area posted there to give you a plastic tab that has a number on it representing the number of items your taking back to the men’s dressing room to try on for yourself?

Thank you all for taking the time to read my article and please feel free to respond to any of the questions I’ve posed to you above.

Visit Transgender Heaven

Sincerely, Jillian




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Jillian Walker

I’m an off and on crossdresser that right now is more on than off. I’m almost 65 years old, married with 3 grandchildren, my lifestyle takes a backseat to the needs of my family. In the last few years I have let the girl side of my personality breathe a little more.

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Helene Bock (@heleneb)
9 months ago

Hi, I was somewhat lucky in the beginning as I was “permitted” to go with my wife shopping – including bras… only once many, many years ago while waiting at the entrance to the fitting rooms carrying my wifes handbag and coat, a “silly” shopassistant asked me what I was doing!!? Another time somewhat amusing, when I went to the cash to pay for a skirt my wife had bought and the cashier asked if it was for me… I got much more confident looking around female clothes as “myself”, not yet at that stage entering into the underwear department… Read more »

Active Member
Patricia Marie Allen (@triciaxd)
9 months ago

I’ll see that and raise you one, or two. Yes, I’ve had that experience, looking and trying not to be noticed. My first upgrade was to not simply walk away when a clerk asked if I needed help. I’d simply say, “I’m just looking.” I can’t count the number of things I bought, just because they were my size. And a number that weren’t, but close and I could squeeze into them. Like you, my shoe size is 12, preferably wide width. I remember early on, when I was trying figure out my shoe size, I bought the largest pair… Read more »

Tara Pink (@tarapinkfancypants)
9 months ago

It usually still takes me a few weeks to build up the nerve to go shopping. I always go dressed in drab as I have never left the house dressed … yet. I only have very limited experience dressing. In any case, this post reminded me of something that happened to me shopping last year. I went to TJ Maxx DETERMINED to buy a few bras possibly a top and some jeans or maybe a skirt. I made sure I went early on a rainy monday when I thought there would be fewer shoppers. Well I walked into the store… Read more »

chloe (@chloe)
9 months ago

I can relate. I finally have had the nerve to try clothes on at the store. What a luxury buying only items that fit and look good. I still haven’t been able to admit they are for me when asked. Shoes I buy online.

Diane McG (@dianemcg)
9 months ago

I wonder if your colleague was wishing he had the guts to shop like you.

Active Member
T.J. Byron (@t-j-2)
9 months ago

We have A l l been where you were in the intimate apparel section looking for our wife( who is at home).
Love the commentary…lived it many times.
Thanks for sharing experiences we have all faced and felt.

Noble Member
Scarlett398 (@scarlett398)
8 months ago

20 Likes and 17 responses…Told ya Jillian! XOXOX Scarlett

Noble Member
Scarlett398 (@scarlett398)
8 months ago
Reply to  Jillian Walker

You’re more than welcome girl friend! XOXXOO Scarlett

Alex Hill (@alexhill)
7 months ago

My core shopping habits haven’t changed that much, only my response to shopping, namely I now enjoy the experience rather than just going through the tortuous motion to get the item I desire. When I started purchasing feminine clothing I would research exactly what I wanted beforehand. During purchasing the item when having to interact with shop assistants (namely at the checkout) I would make some awkward comment like “can I return these items if they don’t fit her”, just to placate my own embarrassment. These days I may browse online beforehand but its a fairly casual affair to see… Read more »

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