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21 Straight Days as Lisa

crossdresser in Ann Taylor dressI was chatting with my girl friend Samantha the other day, and we were talking about our thoughts, feelings, fantasies, etc. from when we were young, a time when we both realized our desires to dress and act like girls but a time that also included feelings of confusion and isolation. The more we talked about our childhood, the more we both realized that our thoughts and dreams were so similar it was almost eerie. It was quite a therapeutic chat, and it further emphasized my belief that my condition--this desire to be a girl--is not unique to just me but is a very tangible emotion shared by probably millions of other genetic males. Goodness, my intent here was not to speculate so deeply; rather, I wanted to share a boyhood fantasy that Sammie and I both had to which many of you can probably relate.

The fantasy was that everyone in the world would disappear for a few days so we could go to the mall, wear anything we wanted, and then freely walk around dressed like girls. I specifically remember treasuring bedtime as a boy because I could lay there in bed and fantasize about being a girl until I fell asleep. At the start of each fantasy, I would take a big eraser like the ones used to clean chalkboards at school, and then I would erase everyone around me so I could enter this dream world by myself. I would inevitably find myself at a department store in the mall where I would pick out a matching set of bra and panties, a new pair of pantyhose, and then a sikly full-length slip with gorgeous lace around the hem. I would next go to the dress section and pick out a silky, floral dress before heading to the shoe department to try on a new pair of heels. Once properly dressed, I would walk back and forth throughout the mall and window shop to my heart's content...until I fell asleep.

As a boy, I of course had no way to make this fantasy come true. The only times when I found myself alone for any block of time during the day was when I was sick and would stay home from school. Both of my parents worked, and while one of them would come home during lunch to check on me, I knew I had a block of time in the morning and then in the afternoon to dress in my mother's clothes as I lay on the couch watching TV. During this time, though, it never once occurred to me to actually fake being sick so I could stay home and cross dress, which demonstrate's a child's inability to carry out his fantasy or fulfill his deepest dreams.

Now as an adult, I still have many of those same roadblocks I experienced as a child that kept me from dressing like a girl and going to the mall, but I am now smart enough to identify opportunities where I actually can fulfill my deepest desire. Due to family obligations, a job, and responsibilities in the community to name a few, these windows of opportunity are scarce, but when they do come, I have learned how to take full advantage of them. Perhaps my biggest window ever opened in July, 2011 when my wife and kids flew over a thousand miles away to spend three weeks of summer vacation with her parents. While I still had my job to attend to, I determined that I would spend the remainder of time dressed like a girl and then blog about my experiences each day.

Looking back on the three weeks, I noticed that I was quite conservative at first sticking to the shadows so to speak as I ventured out as a girl, but as time passed and my confidence grew more and more, I became quite bold in some of my endeavors. I also made great strides in my look during these three weeks finding a foundation and powder that really went well with my skin tone, and I even discovered how to curl my hair just a bit! I was also extremely careful the previous year in regards to preventing obvious male tan lines, and I think that showed during the three weeks as I purchased sleeveless dresses and tops and even ventured out in public wearing all things sleeveless, something I would have hesitated to do before.

Another fun aspect of the three weeks is that I finally purchased a new cell phone with a camera earlier in the year, so I was able to snap candid pics of myself out and about dressed like a girl. Pretty much every time I encountered a mirror out in public, I pulled my cell phone out of my purse and took a few pics. I have pictures of me wearing just a bra with a hanger full of dresses in a fitting room; I have pictures of me shopping in the lingerie sections of departments stores; I have pictures of me driving my car; I have pictures of me trying on shoes; and I even have pictures of me eating at restaurants.

I really got carried away in all things girl, and the best way that I can describe the three weeks is to say they were truly magical. All of my adventures are too lengthy to combine into a single entry in my diary, so after each day's cross dressing adventure, I wrote in my blog about the experience that day and then of course included tons of pictures of me dressed like a girl. Click the link below to start with day 1 of Lisa's most magical cross dressing adventures ever!

21 Straight Days as Lisa!


My Crossdressing Adventures

Meeting Danielle

Swimming at the Public Pool

Getting A Pedicure

"Dress Off" with Wendy

Camping as a Girl

Outdoor photo shoot in my slips

Skiing as a Girl!

Paying Up with Lingerie

Lisa does sushi

Lisa gets Wicked ... Again!

Shopping at Polo Ralph Lauren

Shopping with Heidi Phox

Finding a maxi skirt at last

New Bra at Victoria's Secret

Vanity Fair Outlet and Target

Celebrating July 4th as a Girl

Going crazy at the outlets

Something Pink for Valentines

A Visit to Victoria's Secret

A Trip to the Post Office

Golfing as a Girl

Wearing Pantyhose on an Airplane

Attending the musical Wicked

21 straight days as Lisa





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