Joey’s First Time Crossdressing on Halloween

By Joey

I do not feel like I am a woman. I just like to wear their clothing. 

When I was just getting started, I thought I had to present female in order to be able to wear women’s clothing in public. Therefore, for years I never attempted a public outing in a dress/skirt. The only times that I went out in public as a girl was when I wore a costume for an event and the time I dressed as a girl for Halloween.

The first outing was when my friend asked me to dress as a pregnant woman for an event he was in charge of. There were several people in different costumes. My mother, my girlfriend and a co-worker helped me with my costume, makeup, etc., not knowing that it (not the pregnant part) was a dream come true for me.

A few years after that, in 2001, I told my wife that I was going to dress as a woman for Halloween. She was OK with it. That is not her normal reaction to my crossdressing. This decision led to quite a few amazing new experiences!

Store 1

I went to a store and openly admitted that I was shopping for a dress for myself for Halloween. The salesperson helped me shop. I was able to do something that blew my mind. I was able to step out of the dressing room in a dress! I explained that I was wearing pantyhose for some dopey reason… I did not detect any sign that she knew that I was having an amazing experience. 

I was so nervous. She complimented me on my body and the outfit and reassured me that no one cared what I was wearing. I relaxed some. She had me walk over to the shoes while I was still wearing the dress. I think my soul was leaping up and down during this. I loved that dress, but I could not afford it.

Store 2

I went to a Fashion Attic, which sold after-market clothing. This store was busy. I nervously took a couple dresses into the dressing room. When I hung them on the “No” rack, a young employee saw me. She gave me a playful smile and asked, “Were you trying on a dress?” 

I told her that I was shopping for something for Halloween. She started helping me shop. She spoke too loudly and she did not bother to hide what we were doing. She was stressing me out, but I was also loving it!

I was dress shopping with a pretty, young woman, and having a great time. We laughed. She sent me to the dressing room several times with outfits. I would try one on and then open the door for her to see me. I was way too scared to step out and be seen by the other customers. 

The salesgirl did not appear to believe that this was more than a costume. She took me to the bra section and measured me. I was standing among racks of bras with my arms up in the air while this woman wrapped a tape measure around me. 

A dress similar to the one I wore

No one paid any attention to us. If she could have had her way, my costume would have been me with enormous breasts, wearing a fancy old-lady dress that was covered in shiny beads. I did not want to be funny looking; I wanted to be beautiful.

Eventually we found a light blue sheath dress that had a long, matching jacket. The dress had no waistline. It looked good on my long frame. I peeked out of the dressing room. The salesgirl was helping someone. I waited and waited… 

Suddenly, without warning, the door to my dressing room opened. There I was, a man wearing a pretty dress, standing right at the door, facing a 40-year-old woman who was quite surprised to see me. We were both wearing shocked expressions on our faces. She apologized and quickly closed the door. Unsure of what to do, I said, “Happy Halloween!” as she went to the next changing room.

Eventually, I bought the dress and a bra — my first bra (with a modest B cup). 

I so very much wish I had taken a picture of this outfit. I did not have a digital camera and I was unwilling to take film pictures of me in a dress. (In those days, you had to send film off to be developed and printed.)

Later, I bought some heels at Payless. I still had the wig from my previous outing. So I was ready for Halloween!

Preparation

Halloween came. My wife was willing to go out with me! I convinced her to wear my suit. I had to pin up the legs and sleeves to make it fit. She wore my shirt. I tied a tie onto her. She wore my coat and my big dress shoes.

I shaved my legs and face, got dressed and asked my wife to do my makeup. She did not want to do it. I had to put on makeup for the first time. I think it turned out pretty well! I was wearing beige two-inch heels, skin-toned pantyhose, a light blue sheath dress, a matching duster/jacket, modest makeup and a rather short, curly wig. I was wearing my first dress. It fit me and I felt good in it.

Going Out

Now what? We had nowhere to go. 

We went next door to our friendly neighbor’s apartment and presented ourselves. They were amused. The wife looked at us and saw my wife in a baggy suit and me in a well-fitting dress, with shaved legs and shoes that fit. She shrewdly asked, “Who did your makeup?” 

She knew what was going on. She knew it was not just a costume, but she did not mention it then or later. We laughed and talked for a few minutes and then my wife and I left.

We had nowhere else to go. We were in a small town that did not appear to have any events for us to go to. I was so nervous about this costume that I had not made plans with my wife. I did not want her to change her mind. I did not even know if she would come with me until Halloween day. 

Ultimately, we went to a Blockbuster movie rental store. It was scary and stressful. Having my wife there made it a lot easier. I was not alone. It was a Halloween costume and I felt pretty. People looked at me. It was stressful, but I managed to handle it.

I noticed several guys taking a glance down toward my legs. It was so obvious! The movie place had lots of lighting, so perhaps my hose were shiny. They would quickly look back up at my face so that I would not see them looking. It made me wonder if it is just as obvious when I look at women’s legs or outfits. (Yikes!)

After renting a movie, my wife and I drove around a little and then went home. It was a dull ending to an a fantastic evening. In many ways, it was a non-event. I loved being dressed pretty while in public. No one cared how I was dressed. They looked at me and that was it. It was not a big deal.

Conclusion

Me at the airport

Over 20 years have passed since that stressful, wonderful night. The outfit was lost to a purge at some point. That was the only wig or bra I ever owned. 

These days, I will wear a dress in public occasionally (without the wig, makeup or bra). I will do normal guy things while dressed like this. 

It is still thrilling to be in public in women’s clothes, but it feels more normal. I definitely do not stress/sweat as much as I used to! I no longer get surprised looks from the public. Crossdressing has become like tattoos or wheelchairs. It is different, but not unusual.

My crossdressing is still a secret. My wife still does not like it. I eventually started blogging about my experiences at https://joeypress.wordpress.com and I bought a digital camera so that I would have pictures. 

Over the years, I have gone to barber shops, clothing stores, hardware stores, restaurants, a dentist and even church while crossdressed. I have not yet gone to the theater, a job interview or a wedding while dressed pretty. 

Although my wife would prefer that I was a football player instead of a crossdresser, she still loves me and tries to be understanding. I can only think of one other time that she went out in public with me in a dress. It was another Halloween. We went ballroom dancing. I went as a man in a ladies’ black dress and she went as a woman in a men’s suit. That time, though, we bought her a suit that actually fit!

Wearing Venus

Frequent femulator Harvey Korman on television’s The Carol Burnett Show.