Haircut and Other Errands

11/4/2019

I took a long lunch break and completed of a list of errands.  I decided to wear some heels for this outing.  I also wanted to wear my new cardigan.  I wore my black dress, my new brown and black cardigan, my new Spanx pantyhose, and my bootie heels that I bought for a party.  I have only worn these shoes a few times.  I feel a little bit ridiculous in them because of how high they are.  I am a tall man in flats!  Well, this man in a dress and heels went on a marathon of outings in this outfit.

Apparently, I was the only one who felt like my shoes were silly.  Everyone else thought they were fabulous.

Shopping While Crossdressed

10/22/2019

I had a gift card for a department store at the mall.  I had visited the store a couple times in menswear looking for something to buy.  I decided to go back there dressed pretty so that the clerk could help me with some understanding.  I arrived just as they opened to avoid the crowds.  I wore my black skirt, my purple blouse, and my black cardigan.

Meeting, Lunch, and Errands in a Skirt

10/16/2019

I had another scheduled meeting with my coach.  I decided to dress pretty for this meeting as well.  I also needed to go to the bank.  I wore my gray skirt and my black and white blouse with my black wedge heels.

Fellowship Time at Church

10/14/2019

I was able to get a copy of a video of the church service I recently attended.  During the fellowship time, the cameraman panned the room.  (I’m the guy in a skirt with a blurry head.)

One thing is VERY interesting to me.  There is a woman on the right side of the screen who ushers her kids out of the row so that she can get out.  Then she comes over and waits briefly, and shakes my hand.  Afterward, she returns to her seat.  This is the same woman who I saw before the service look across the aisle at me.  She could see my legs and my wedge heels.  She had a look of realization.  No matter what her initial reaction was, this nice woman was willing to come up to me and greet me.  That made me feel so special when I saw that!

In fact, I feel special every time I see it.

Very Social Outing

10/2/2019

For the past year and a few months, my schedule has been fuller than usual.  It has been tougher for me to find time to go out crossdressed.  I had a scheduled meeting with a person who knows that I am a crossdresser, so I decided to wear something pretty on my next visit.  Therefore, it would fit into my schedule.  I wore my beige skirt, a black and white striped top, a black cardigan, and my black flats.  Unfortunately, I did not remember to take a picture of myself.

Sunday Morning at Church!

9/22/2019

I had a Sunday morning to myself and I visited a small, conservative, Evangelical, country church similar to the church I attended for about half of my life.  I drove over an hour to where this church was located.  I wore my new khaki skirt, a red top, and my black and gray striped cardigan with my black wedge heels.  I felt pretty.  However, I was nervous…

A Vacation Outing

9/22/2019

While I was on a recent vacation, I arranged with my wife to take the kids and give her some free time.  Later, she took the kids and gave me some free time with the understanding that I was going to go out dressed pretty in a skirt, etc.  She does not love it that I am a crossdresser, but she understands a little.  Her parting words for me were, “Have fun, and don’t do anything stupid.”

I wore a rather subtle outfit: a denim skirt that falls above my knees, a grey and white striped shirt with an unbuttoned collared shirt over it.  I wore nude pantyhose and white Keds sneakers as well.  I think the outfit was not obviously unusual.  Based on my experience, I believe most people could not tell that I was not wearing shorts.