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We are in the middle of a week of rain, but it is Sunday, so I invited my wife to go shopping at a mall that we have never seen before. She wanted to go out anyway, so she didn’t need prodding.
But what to wear? I don’t have subtle enough shoes yet, so I padded my hips and behind and wore my favourite pleated black pants. They have wide hip flares and reasonably deep pockets. I chose a shiny black blouse that she had never seen before, put on a soft bra, and slip my breasts into the pants pockets. Under my pants I wore good, black pull up stockings that could be mistaken for black socks. Wandering around the apartment like this while she was getting herself ready, she briefly observed me, but didn’t say anything. Cool! So far… Slipped on some grey cloth men’s loafers and a warm enough zippered sweater jacket. Ready to head out. Nothing was said until we reached the mall, then she got distracted with her own shopping.
While she was looking around, I saw some women’s shoes, which were nice and all, but nothing over size 10, typical of a store with tight inventory controls, so I searched for other gems. While out of sight of everyone, I undid a bottom and slid in my breasts. They aren’t big, just enough to give shape. My sweater was left open loosely, which helps to camouflage what is going on.
Then I saw a table covered in various denim shorts! Bingo! The store is Urban Planet, of which I had never been in one before, so I wasn’t familiar with their sizing, but that didn’t really matter because… I had my measuring tape. Size 9. Looking through the various colours, I picked out two MOM shorts. My wife pointed to a store across the isle and was gone. Went to the cashier, paid for two women’s shorts and she didn’t blink an eye.
We found another clothing store that was unfamiliar to us – Designers Row. As it turned out, they sell remainders, end of lines. We wandered around separately and I searched out the women’s shoes again. I found the largest sizes and they had only one kind of shoe in size 12, in black and a tan. The heel is higher than I wanted, but when I put them on my feet, they put a huge grin on my face. They were so comfortable, with a sock on top and a cushy footpad. My feet would never forgive me for not getting them, but I put them back on the shelf and helped my wife make some decisions. I pointed to where the fitting room was and while she took off, I tried on a nice sweater that she suggested for me. The sleeves were that much too short.
While making a quick diversion to the washrooms for my wife, I saw a second huge store of Designers Row and saw that they had even more shoes. Made a mental note to return. Then my wife and I continued to peruse more stores.
At one point, either I made a move or my wife leaned over and I saw her glance towards my chest. I had purposely left an extra button open, so I don’t know what caught her eye, but something caught her attention. She didn’t say anything, though.
Eventually, while my wife was still in another store, I went back the second Designers Row and was greeted by a sales clerk. She asked if I was looking for anything and I said yes – large ladies shoes. That flustered her, a bit, but she told me where they were and I found another sized 12, 3″ heeled skin-coloured ankle-strap pair of sandals. This is when the thin stockings and slip-on shoes come in handy. I quickly slipped off a shoe and found that my foot slipped in comfortably, did the strap up and tested it out (the other shoe couldn’t be put on). So I put them back in the box and went to find my wife, since she had no idea where I was. I brought her to the store and I pointed out a few nice things for her, but she declined them. So I started looking around for myself and found a very interesting pair of Calvin Klein deep blue, stretchy denim pants with a 32″ long inseem. Yes! Perfect to hide high heels! Took out my measuring tape and found another gem. I had told my wife that I found a pair of shoes, but she didn’t show any interest in that, so I tried them on again, just to be sure. Put them under my arm and followed my wife around some more. Time was running out before the mall would be closing, so I went to the same cashier as earlier and paid for my finds. I am certain that, by now, the clerk was bursting with curiousity, but we completed the sale and went to get something to eat.
I finished eating more quickly than my wife, so I said for her to wait at the table while I went back to find the black sock shoes. Tested them again, just to be sure, and paid for them just as the doors were being locked. I really didn’t want to disappoint my feet!
Collected my wife and went home. As usual, she fell asleep on the way home. At home, nothing was said by her about how I was dressed (I looked mahvellous!) or my purchases. Now that she fell asleep, I tested the fit of everything. Not one problem. The shorts fitted, the Calvin Kleins are amazing because they are of a stretchy material. Oh the things we learn.
So, why am I describing all of this? It was a test, partly to see how observant my lovely wife was and if she would say anything good, bad or otherwise about how I was dressed or what I was buying. It was also a test to see how an obvious male buying women’s clothing would be accepted or not. It also was another practice run of using my measuring tape method. Everything passed with flying colours!
My wife was with me on a shopping trip, she saw me buying women’s clothes and didn’t complain. The only thing that she keeps on saying is that she doesn’t want me to wear my high heels when we are out together (I am desperate to find some appropriate low-heeled pumps), but if I keep things subtle as with some of my other clothes hiding them, who knows how long she will resist?
It was a good but rainy day.
Thanks for sharing your adventures. Very bold. If only we didn’t have to play this cat and mouse game with our wives.
Thanks for the measuring tape trick…so easy to check sizes will fit that way.
I would caution that just because a wife doesn’t make a comment in the moment that doesn’t mean you received unspoken acceptance.
Males tend to voice objection to things we dislike right as we see them. Women on the other hand tend to think things over before speaking and to guys it feels like a trap has been sprung on us.
Don’t worry, I am learning as I go along, too. We spoke about things more after she had a snooze. Things are encouraging. It looks as if I may have to keep repeating, for a while longer, that I just want to look good and that women’s clothes look better than men’s clothes do and that I don’t want to transition.
I also forgot to mention, above, that I wrote about what I did and how as encouragement for others here. Maybe a reader could be emboldened to step outside themselves. At least that was my hope. There is a lot of encouraging going on in this forum and this was mine for the day.
Good for you, thanks for sharing. I was underdressed shopping with the wife last year and we went to a Jockey outlet store. I picked up 2 nylon briefs on sale (my size) and told her I wanted these. She just shook her head and said OK. Same thing a couple years earlier at JC Penny lingerie clearance rack I picked up a mint color matching bra and panty set. The only 2 times I ever bought women’s things for me with her. We’re basically DADT.
If you want larger size womens shoes I use zappos. never had a problem. I needed womens 13
had to pratice wit 4inch pumps but got it down
Today was another shopping adventure with my wife, this time with a surprise ending for both of us.
My wife doesn’t want to stay home on her days off and this time she wanted to go out of town to a mall that she knew about. She saw me put on my thigh highs and other underwear, but I also wore some new shoes with pink, etc., so there were no real surprising things going on, or so she thought. It was cool enough that I wore a jacket, but I took that off when I arrived at the mall. That clearly put my chest on display, but my forms were the smallest that I own. You know, being subtle.
I showed her some pink shorts that she thought wouldn’t fit me, but I pulled out my measuring tape and said that they would. I also selected a pink top (pink is her all-time favourite colour) and told her that I needed an A-cup bra and found one.
We moved on to other stores and she found a button front dress that I helped her to get her size right. She was also wearing her heels in public that I talked her into getting, for the first time. She was a champ in them.
After arriving at home we both put on a bit of a fashion show with all of our new finds. That’s a first, too. When all was said and done I gave her a good hug. That’s when she noticed my breasts for the first time. I said that you’re kidding me, but no, she went all day beside and facing me without noticing them, so we had a good 🥳 about it all. Either I am being way too subtle or she really couldn’t see a tree in a forest.
One step at a time…
During our Victoria Day holiday, we went to see Kensington Market for the first time since COVID started. I came across a small store that features large women’s shoe sizes, including all half sizes, up to 16s. Pleaser and Fabulicious brands are supported / stocked.
I couldn’t spend a lot of time looking, but I will go back soon, to get fitted, since I saw some low-heeled pumps.
If you are in this interesting Toronto market area, check out Aunt Thelma’s store. I saw more wide shoes there than any Torrid store that I have been in, and she seems LGBTQ friendly.
Edit: Today, I returned to Aunt Thelma’s, since I had the time and freedom to check out Ellen’s shoes. I settled for a simple low-heeled pump, but I am going to have to try to make it fit better. Her clients include a variety of the drag / crossdresser community, so if you are in Toronto, check the store out.
While I underdress often and therefore shop with my wife while underdressed, I have never shopped for feminine things with her. While she is fine with me underdressing in public, she prefers I keep my outer dressing be done in private. So, while I will shop en femme solo, I do not shop for my femme things with her. She knows I shop for femme things since I have plenty of items in my closet and drawers she just would rather not be part of the shopping.
My wife likes to shop at clearance stores, such as Winners. She complains that she sees some nice clothes, but when she returns a following day, that they are gone. If I see something that I want, I learned from her to make buying decisions right away. I go to the cashier on my own most of the time, so far.
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