Ten Years Ago

1/1/2022

Back in 2012, ten years ago as of this writing, I decided that I wanted to collect the stories of my crossdressing experiences onto a platform that I controlled. I collected experiences that I posted on the two places I primarily posted in those days:

• LAUF (Legwear As a Unisex Fashion) forum, a forum where men write about wearing pantyhose, tights, and other forms of “legwear” with their menswear. (They will block you if you talk about wearing skirts, or being a “crossdresser”, etc.)
• crossdressers.com, a forum where mostly male-to-female transgender people and crossdressers write about their lives.

I collected all of these stories and attributed dates to them the best that I could. Then, I started backfilling with stories of my earliest crossdressing memories. Eventually, on February 29, 2012, I posted my first post onto this website, joeypress.wordpress.com.

2021 Christmas Shopping Outing

11/30/2021

Every year, I go Christmas shopping while dressed pretty. “Dressed Pretty” == me, as a man, wearing a dress or some other women’s wear. I normally go to a town about an hour away. Last year, I went to a town that was slightly closer, but smaller. This year, I went to a new town because it had a better weather forecast. I wore a black dress, black pantyhose, black shoes, and a deep red cardigan. I have crossdressed in this town once before, when I bought my car. Today’s trip was not very pleasant. There were plenty of very pleasant experiences, but there were some negative ones that overshadowed the whole day. Probably, my attitude was what made it unpleasant, not the negative experiences…

Tights in a Masculine Halloween Costume

10/30/2021-10/31/2021

My family went to a few Halloween events. My kids asked me to dress in a super hero costume that I have used for several years. This costume includes black opaque tights. This year, I wore my black Hue Luster Tights instead of the black tights that I normally wear with this costume. The normal tights are matte and more opaque. No one in my family seemed to notice the difference. No one in public mentioned the tights or seemed to pay much attention to them.

Doing Manly Errands in a Skirt

10/26/2021

I have not had a significant outing in quite a while! Today, I had a reason to drive across town. While I was out, I was determined that I was going to dress pretty and do something — anything! Where I live, in the autumn months, the weather gets significantly cooler. This causes the leaves to change colors and fall. It is a beautiful time of year. Women (and some men) dress in more “autumn colors” including orange, and various browns. I selected an orange blouse that is very autumn-appropriate with a denim skirt, white Keds sneakers, and a white cardigan sweater. While I was out, I got more and more daring.

My Thoughts On Passing

10/9/2021

Recently, Sue Richmond and Susan Miller wrote posts about passing. “Passing” is what a crossdresser or transgender person calls it when they go out in public and someone perceives them to be a woman. Used in a sentence: “The transgender person successfully passed herself off as a woman.” Basically, to someone who is trying to present a different gender than their biological gender, passing is the report card. Since I present male when I wear women’s clothes, yet I still go out in public, I have an uncommon perspective on this topic. After reading Sue’s and Susan’s excellent posts, I decided, “I should weigh in on the topic as well.”

Eating Fast Food While Crossdressed

October 7, 2021

I had the house to myself for three hours. I needed to drive to town to take care of an errand. I decided to wear something pretty and run my errand. Later, I decided to eat supper while I was out. I wore a black knee-length skirt, my nice, orange, autumn blouse, a brown and black duster sweater, and black wedge heels. I present male when I crossdress. So, I was a man in a skirt in public. It was a nice experience, and I received a compliment!

Our First Date!

9/9/2021

My family went on a one-week vacation. I brought an outfit, just in case I had an opportunity to have a crossdressed outing. On each of our previous vacations, I have always had at least one opportunity to crossdress. These days, my kids are old enough to stay home and let my wife and I go on a date. I conceived the idea to ask my wife if we could go on a date while I wore something pretty. (When I crossdress, I incorporate women’s clothes into my male wardrobe. No makeup, bras, wigs, etc. My children are unaware of my crossdressing.) I asked my wife if I could wear something pretty (women’s clothes) on our date. I said it was not required. I added that it would mean a lot to me if she would do this with me.

Inside the Bank in a Skirt and Heels

8/4/2002

We had a collection of checks that needed to be cashed. I packed a long, stretchy skirt with a black and white, brushstroke pattern, a black top, a red cardigan, and my black heels for the errand. My bank is allowing customers to come inside again, for now. So, I left work, changed into my pretty clothes, and looked forward to seeing my bank friends in person for the first time in over a year.

Out and About Donating Blood

7/28/2021

The blood bank has been pinging me pretty hard about donating. Apparently, the blood supply is critically low. The last time I gave blood was the first time I ever donated blood while dressed pretty. Their need, plus my lovely experience last time, made me excited about going again while crossdressed. I wore a black blouse with white accents, a khaki skirt, nude pantyhose, and black wedge heels. It was very nice. It was better than last time! Three women complimented me, one man sort of hovered around me, and later a woman and her granddaughters talked to me.

I Was Called Beautiful

7/5/2021

I have not been able to do much crossdressing for months. It has been too inconvenient for me to go far from home and wear pretty things where acquaintances will not see me. I have squeezed in a run for milk or wearing some invisible pantyhose to the gym. I have been itching for an opportunity to go out in public while crossdressed.

I have offered to my wife to do our grocery shopping for some time now. It just has not happened for two reasons. 1) My wife is hesitant to have me out in public in womenswear. 2) Our family is quite busy (our kids are to that age where they are doing things out of the house and we help them).

Today was a national holiday and I was off of work. My wife offered to take the kids to their events, and she let me do the grocery shopping. I had the house to myself that morning. I bleached my leg hair, showered and shaved my face, got dressed, packed some men’s clothes for afterward. I got dressed in a black top, a black and beige printed skirt that I bought at a yard sale, and my black wedge heels. I walked out to my car in the garage while dressed pretty and left my house. I went to four different places as a man in a skirt. I had an excellent experience!