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Grocery Shopping

February 12, 2017


In a previous post, I described a Day Off Outing that I went on.  During this outing, I did some shopping for my wife and I.  Later, I discovered that I would have to take a few items back for a different size.  So, I planned a return trip.  I set off after lunch and changed into a black knee-length skirt, off black pantyhose, black flats, and a red top.  I also brought a purple sleeveless top to wear, but I forgot to bring a white, button-up shirt to wear unbuttoned over the purple top.  Like usual, I was presenting male — no bra, no makeup.  Just a man in a dress.  If I had done only the things I had intended to do, then I would not have gone over my planned schedule.  But, I did…

Shoe Store
My first unplanned stop was a shoe store.  I and an older woman were the only customers.  She and I shopped on the same row.  Other than saying hello to me before I left, we had no interaction.  The sales people spoke to me as the walked down my aisle, but did not take any interest in me.  At one point, I saw two young men, with piercings and flat-billed hats walk along in front of the store.  I thought, “I hope they do not come in here.”  I presumed that I would have felt awkward around the two young, “grunge” styled men.

Hobby Store
Near the shoe store was a sort of hobby store.  I walked in and discovered that the two “grunge” guys were in the store talking to the main employee, a man.  There was one other male employee sitting at a table.  I looked at the two grungy guys and they looked at me.  I discovered that one appeared to be either a trans-man or a woman trying to be androgynous.  I heard this person speak in a female voice, but all other indicators suggested that the desired presentation was male.  I relaxed about those two!  They exited shortly after I arrived.  While I was browsing, the main employee came to help me.  He was in his 30s.  He had a few uncommon piercings.  The other man working in the store was sitting at a table.  He had a lot of tattoos.  Both men treated me with respect.  Eventually, we talked about hobby projects that we are working on for about ten minutes.   This was also an unscheduled stop.

Ladies’ Wear Store
For my next unscheduled stop, I walked to a ladies’ wear store in the shopping center.  I was looking for a cardigan.  Due to the time of year, they did not have any cardigans.  I left.

Fast Food Restaurant
It was time for me to eat some lunch.  Since I was behind schedule, I went to a hamburger restaurant.  I walked across the front of the store to the door.  Two young men, possibly teenagers, were on either side of a car talking.  One was facing my way.  I looked over at them and saw that both were looking at me.  I waved hello and they returned to talking.  In the restaurant, there was one customer.  His back was to me the whole time he was there.  The employees never looked my way until the counter blocked my skirt.  I think they never saw me either.  I ate my lunch in peace.  That was my first scheduled event.

Grocery Store
Going to the grocery store was a planned activity.  Years ago, I went to the grocery store in shorts and nude pantyhose and I did our family’s grocery shopping.  I was so nervous.  I kept the shopping cart between me and most people.  As I recall, no one showed any sign of noticing what I was wearing.  It was a major event.  I loved that experience.  While anticipating this far-from-home outing, I decided to do our family grocery shopping in a skirt.  I have been in grocery stores in skirts before, but it was only for a couple things early in the day.  This trip would be during the day.  This trip would be long.  I assumed I would keep running into the same people as I traveled the aisles, like normal.

I scheduled my day so that I would go to the grocery store while school was in session.  The store was rather empty when I started.  It did not stay that way.  I had a long list of things to buy.  I walked down every aisle.  Other than the initial look that people give me to see what is before them, roughly everyone treated me like I was dressed normally.  This store is in a small, conservative town.  Regardless, they treated me like larger towns in which I have crossdressed.

As I said, I walked down every aisle.  Normally, I felt comfortable and welcome.  There were a few occasions where either people reacted differently to me than described previously, or where I felt like hurrying away.  One time, a man and his teenage son walked down the aisle toward me.  The man seemed like a serious or stern man.  The boy was rather stoic.  Perhaps he was somewhat “stiff” from trying not to react to me.  After they passed me and started turning up the next aisle, I looked their way.  The man was now looking at his son with an amused look on his face.

Another few times, there were children that I wanted to avoid.  The only significant one was when a man with two girls were on the aisle with me.  The girls were between nine and twelve years old.  I kept the cart between us and they did not see my outfit.  Later they were on my aisle again and I could not avoid being seen.  I left the aisle promptly.  I heard them giggling.  I assume they were probably giggling about me.  While I was on the next aisle, they peeked around the corner to get another look at me.  I saw them and I turned my head toward them.  We kind of looked at each other for a second.  I gave them a slight smile and a short wave.  They stopped staring and “became distracted” by something nearby.  Perhaps they took more looks at me, but I did not bother to find out.

That is about all that happened.  There was one customer whom I saw on most aisles.  She is in the picture below.  When she first saw me, she gave my outfit no reaction.  She never acted like she minded being around me.  We never spoke.  I feel like this outing might sound boring.  But it was not.  I loved it!  I want to do all of our grocery shopping in a skirt now!  Some customers only nodded a “Howdy,” others smiled and said hello more like normal (I live in a friendly part of the world).  I loved this part of this outing because I was a normal guy in a normal place doing a normal thing while wearing a skirt.  That was rewarding.

There was one non-normal thing I did…  I brought in my camera and took a couple pictures of me in the store.  I did this because a couple people have asked me to post a picture.  It really feels odd using a camera in auto mode to sneak a picture of myself.  When I walked away from my cart for the first picture, I realized that I did not turn off the flash.  “Oh, no!”, I though.  “Anyone nearby is going to know I am taking pictures of myself!”  Fortunately, the flash did not go off.


Small Clothing Store
I was still looking for a cardigan when I went to a small clothing store.  Again, this was not scheduled.  They did not have cardigans.  I walked around the store looking.  I came upon a family.  There were two little children that I did not anticipate.  They were probably two and three years old.  I was at a rack and both kids came around the rack on either side of me.  The older child, a girl, stopped and looked at me.  She said to the roughly fifty year old woman who was with her, “He is wearing a dress.  Why is he wearing a dress?”  She said it in a hesitant way as though she did not know if it was inappropriate to say out loud.  The woman said, “I guess because that is what he likes to wear.  Don’t you like to wear dresses?”  A few minutes later, the woman spoke to me about the kids, but not about the girl’s comment.

Department Store
I went to a nearby department store.  Again, unscheduled and again looking for a cardigan.  At this point, I am not going to get home when I wanted to.  In the ladies’ section, a sales girl tried to help me.  She was in her early twenties.  This young woman was very nice to me in spite of my clothes.  While talking to her, I spoke negatively about my extra weight and later about my shoulders, etc..  Each time, the sales girl had something bad to say about her weight or shoulders, etc.  In my opinion, she looked like a pretty woman.  She smiled a lot, which is the best makeup.  If she is so wrong about the negatives she expressed, then maybe I am wrong about my negatives too…

I asked the sales girl if she would take my picture.  I mentioned that I wanted the picture for my blog.  She asked for the name of my blog.  That was a bit of a moment for me.  I do not give out my blog name in person.  I try to keep my blog more anonymous than that…  I gave her my blog name.  I assume she forgot it by the end of her shift.  What I know for sure is that by this point, I was late, and I still did not have a cardigan.


Department Store 2
I said to myself that My next stop needed to be the store where I needed to return some items.  However, on the way, I stopped at another department store.  I shopped around and found a few cardigans to choose from.  I asked another customer for color advice at one point.  She politely helped me, but I think she was a bit surprised to be helping a man in a skirt.  Her surprise did not limit her help.  I selected a cardigan.  I worry that it is too feminine for my style.  I got in line to check out.  There was an older man talking to an older couple.  They must have been friends or neighbors.  I was standing in plain view not too far from them.  At some point, the man, who was talking, looked my way.  He totally lost his train of thought.  He paused for a couple seconds trying to remember what he was saying.  His friend spoke up changing the subject and saved him from the moment.  That is a decent friend!

Outlet Mall
Finally, I made my way to the outlet mall.  I changed into my purple sleeveless top and the new white cardigan.  I returned my items to the store at the outlet mall.  The same employees were there that served me when I went the first time.  I was feeling good in my black skirt, purple top, and white cardigan.  I thought the outfit was pretty.  The sales girl said it looked good.  I left the store and took a lap around the group of stores I was in and returned to my car.

When I got home I was over an hour later than I intended to be.  My wife was annoyed at me for being late.  Getting home on time from outings is a problem for me.  I have too many “just one more” moments.


From → True Stories

  1. Rachel permalink

    You look so pretty. You outfit looks great! The color combo of your top and skirt is perfect. I have to add that your shoes are gorgeous. To top this all off you are so smart and brave. …

  2. That was a fantastic story; and I envy your relationship with your wife. I so wish my wife would be encouraging and accepting of my crossdressing. I keep my body and legs smooth shaven, and would love for my wife to encourage, even better, order me to wear sheer nylons on a regular basis for her inspection, seeing as I keep my legs so feminine. Thus; I would enjoy a dominant side to her nature.

    • Perhaps you misunderstand my wife’s perspective on this. She does not encourage me. She is tolerant at best. My wife loves me and lives with the fact that I am a crossdresser. She would rather I stop crossdressing. The most encouraging thing she has ever done is to say she is glad I enjoyed myself after I have gone on an outing. We have a pretty good relationship. The dressing is hopefully a side issue.

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  1. Grocery Store Outing | joeypress
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