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Challenges of Crossdressing 24/7

I had quite an eye-opening experience a few weeks ago when I was able to take a short vacation as a girl. This little excursion was just for one night, and the destination was also close enough to where I could drive, so that meant I would be a girl 100% from the time I left my house until I returned late the next day. In preparation for this journey, I was able to pack an overnight bag, and oh what fun I had doing so! Even though the trip was just for one night, I packed four pairs of panties, three bras, six tops, two skirts, two pairs of shorts, two pairs of shoes, and a sleeveless dress. I had always heard about women over packing for trips and laughed at such jokes along with everyone else, but now I was actually experiencing the sensation for myself. I realized that while my vacation was just for two days and one night meaning that I would likely only need two outfits, just thinking about the possibilities was enough to make me pack enough clothing for a week's journey.

As part of this packing process, I didn't allow myself to bring a single guy article of clothing, and since I left my house as a girl and drove to my destination as a girl, I wasn't wearing any guy things as I traveled. The result was that no matter what situation I faced while on my mini-excursion, I would have to face it as a girl, and at first thought, one might think that that is not such a big deal, but once I actually got on the road and reached my destination, I quickly learned that only packing girl things was going to pose a challenge to me because I found myself in multiple situations where I would have preferred to handle things as a guy but couldn't because I didn't have the clothes to present myself as such. And so I thought I would reflect on what it means to truly be a girl 24/7 because while I have used that expression many times in the past, I truly wasn't a girl 24/7 because I always had my guy things at home to use as a backup just in case a situation arose.

The first incident that occurred where I would have been tempted to dress like a guy came after I arrived at my mountain condo. When my wife is away from home, we always schedule a time to video Skype with each other so I can see her and the kids, and on that first day, we planned to talk just after my arrival. We don't have an internet connection inside of our condo due to limited access, but there is a general building at the facility that houses the main office, an exercise room, a conference room, etc. and here they have free wireless internet for the tenants. That meant that in order to Skype with my wife, I needed to not only go over to the main building, but I had to talk in a voice close to my guy voice even though I would be dressed as a girl in full make-up and hair. I wasn't aware how crowded the facility would be, but I had no choice. I had painted myself into a corner, and I had to carry out this errand as a girl.

Fortunately, the internet isn't that strong in the mountains, and so my wife and I turn off the video portion of Skype since it tends to freeze up with a weaker connection, but I still had to be discrete looking like a girl and talking close to the way a guy would sound so my wife wouldn't be suspicious. I wonder if I would have had a change of guy clothes with me if I would have made that call as a guy, but I'm glad I was forced to make it as a girl because it made me get out of my comfort zone and push myself a little bit further. Incidentally, the call went quite smoothly until an older couple came in and sat right next to me so they could access their email and read it out loud to each other. I stood up when they sat down to create a little bit of distance, and the gentleman said, "you don't need to leave on our account," and so I whispered back at him pointing to my iPad, "I'm on a call." I gave him my best smile and he nodded as if he understood, and I don't think he suspected anything regarding my true gender.

The next incident that arose came after this call when I returned to my condo and prepared to fix dinner. I had brought a leftover casserole with me, but I didn't have any veggies, and I'm quite a stickler when it comes to eating a balanced meal, and so I really wanted to run to the local store and pick up some broccoli. Once again, this was an errand that I really hadn't planned on, but if I wanted the broccoli, I had to go purchase it as a girl, and so that's exactly what I did. For my drive up to the condo, I was dressed quite nicely wearing nylons and black ballet flats, and so I changed into a more casual outfit to go to the store, but I still remember trying to talk myself out of the excursion to the store because it wasn't on my list, and I'm usually quite careful when going somewhere crossdressed as a woman for the first time.

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My Crossdressing Relections

My Cinderella Story

Autumn Photo Shoot

Mommy memoirs from the ballpark

Psychological need for bras

Crazy night at the ballpark

In the mood for pink

Long overdue photo shoot

A girl and a flower garden

Signs of a Girl

Challenges of being a girl 24/7

Quiet Picnic as a Girl

Why My Bra and Panties Rarely Match

Dimensions of being a girl

Pantyhose here and there

Connecting with my cross dressing roots

My slip is showing

Crossdressing and Halloween

Sunday Morning Walks in a Dress



My Biggest "What If?"

Mornings as a Girl

My Mother and My Crossdressing

Motherly Feelings While Crossdressed

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