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Transgender Vacations

JJ Hart
4 min readJun 15, 2024
Image from Ezequio Garrido on UnSplash

Since it is summer time, it is vacation time around here. Spoiler alert, this post is not about flying these days as a transgender woman or making it through airport check points unscathed. It is about ground based transportation. I did all the flying I wanted to do at an earlier period in my life when the military flew me all over the world.

My problems with going on any sort of vacation at all began when I was cross dressing as a man on a vacation to Michigan one year with my second wife. Very early on, I began to feel the pressure coming on when I couldn’t go out in the world as a novice transgender woman. Then, I began to resent the fact I needed to be a guy at all and I wanted to be a woman with all my being. By doing so, I started to grow quiet and introverted which alerted my wife that something was wrong with me and she started to pry. After all, we were on vacation from two successful jobs we liked, were blessed with my daughter we both loved and a 1860’s restored house we lived in. Ideally, we shouldn’t have any problems but I did.

As I internalized my gender issue, I never answered her questions as to what was wrong. There was no way I was going to tell her I would rather be spending my vacation time as a woman rather than my male self. So I shut up and did my best to change or hide my feelings. By doing so, I was able to salvage what was left of my vacation.

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JJ Hart
JJ Hart

Written by JJ Hart

Thanks for stopping by! I am a married Transgender veteran author and blogger. I write in the hope of helping others with similar gender dysphoria

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