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Enjoy my cross dressing adventures on this page. Click the cross dressing links below.

21 straight days as Lisa

Les Miserables en femme

A night at the opera

Near-miss with the boss

My wife's reminder

Tights in Tokyo

Propositioned while cross dressed

Errands and a picnic

Shopping for bras en femme


Here's another cross dressing adventure where I go outside as a cross dresser.

My First Photos in Public while Crossdressed

As a cross dresser, I notice the tiniest details of women's' outfits on a daily basis. If they are wearing pantyhose, I try and determine what brand and shade they are since I've tried most brands myself. I notice whether or not their bra fits properly and is the correct size, and I notice each article of clothing they are wearing and whether or not it's coordinated well. One of my favorite things about venturing out into a public place is the chance it gives me to observe women and their fashion.

Sometimes I will come across a woman or girl who is wearing the cutest outfit, and something clicks inside of me that makes me want to put together the same outfit for myself, so the next clothing that I shop for as a cross dresser is largely determined by these experiences.

During the Christmas holidays of 2008, I was at a winter resort area where our family owns a timeshare, and while we were relaxing inside of the main lodge area, a family walked in that included a young girl probably around the age of 12 or 13. She was dressed in a black turtleneck, a red plaid skirt that hung just above the knees, and black tights; the perfect outfit for the holidays. I don't remember if she was pretty or not, but she sat down on a sofa near the Christmas tree with her legs crossed and perfect posture fully enjoying the moment of being a girl and dressed in such a cute outfit. Her younger siblings were running around, and her parents were looking at different displays in the lobby, but she was just content to sit there like a proper young lady who was dressed the part.

I often wonder what it would have been like to grow up as a girl and be able to wear such cute outfits in public anytime I wanted, so as I observed her sitting there I still remember an aching feeling inside because I wasn't able to experience life as a girl when I was her age. For some reason, the situation made such a big impression on me, and I had one of those moments where I realized that even though I could never experience life growing up as a girl, I could still dress up in a similar outfit and sit on the same sofa like a lady.

a cross dresser sitting like a lady in a skirt and tightsAnd so that's what I determined to do prior to Christmas the next year. I already had a black sweater that was perfect to wear in winter, and I already had at least three pairs of black tights, so all I needed was a red plaid skirt to wear. I shopped on eBay for one and found the perfect skirt made by Liz Claiborne size 14p. I checked my calendar and determined a day when I would be able to visit this resort and dress up in my Christmas outfit and have my picture taken while sitting on the couch in front of the Christmas tree just like the young girl I had observed the year before.

I was so excited as the day approached, and fortunately everything came into place so that I was able to carry out my wish. I drove to the resort wearing bra and panties under my male clothing with suntan pantyhose and made it to the room accessible to me as part of our timeshare. I put on my makeup and changed into my outfit in good time, and before I knew it, I was ready to venture out into public and sit in the lobby near the Christmas tree dressed in my red plaid skirt and tights. Although I have cross dressed in public too many times to count, this would be the first time that I would actually photograph myself in public while dressed as a woman, so it added some anxiety to my adventure.

When I was satisfied with my appearance, I grabbed my camera and headed outside for the walk through the parking areas towards the main lodge. It was a clear day outside, and it felt exhilarating to be dressed in a skirt and tights and walking outside on a winter day. There weren't too many cars or foot traffic nearby, so that helped to calm my nerves, but I wasn't sure what it would be like inside of the lodge. I picked a weekday where I knew there wouldn't be too many people around, and I entered the lodge relieved to see that it was largely empty. I walked a cross dresser at a public photo shootover to the sitting area and noticed right away that they didn't set up the Christmas tree this year, but I was already committed, so I made my way over to the line of sofas and sat down with my legs crossed.

After observing my surroundings for a few minutes, I set my camera on the back of a nearby couch and began taking pictures of myself cross dressed in my Christmas outfit. I didn't want to stand out and have anyone come over and offer to take the picture for me, so I was very cautious at first. However, everything was going so well, and I was enjoying just sitting there on the couch that I decided to walk over in front of the fireplace mantle and have my picture taken there.

Everything was a success, and I was able to take plenty of pictures of me in the lobby cross dressed in my holiday outfit, but I must have been more nervous than I thought because when I got back home and loaded the pictures from my camera into my computer, I noticed that my eyes were peering this way and that in many of the pictures. I must have been quite nervous because every movement in the lobby seemed to grab my attention; even when I was in the middle of shooting a photo. At left, I have posted a picture of me looking in the wrong direction, obviously distracted by someone walking nearby.

All in all it was a fun cross dressing adventure, and I was more than pleased with the way the photos turned it. I loved them so much that I even used them for my Christmas card in 2009. It's small experiences like these that give me more confidence for the next outing. The important thing to cross dressing in public is to be confident in yourself and not care what anyone else thinks. I was so enamored by that young girl properly sitting on that sofa dressed in her holiday outfit that I just had to try it for myself.

Click here to see more poses of me dressed in my black sweater, red plaid skirt, and black tights.


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