I Went ‘Commando’ in Puerto Rico and Other Travel Adventures That Pushed Me Outside of My Comfort Zone

Bugs. They are one of the reasons that at the age of almost 30 I still felt uncomfortable even going to bed with no undies beneath my pajamas much less going out into the world “free as a bird.” I was afraid that some kind of dreadful bug would find its way up my leg without notice and lodge itself in my “forest” and, at some point, make it inside of my… The thought made me quite nervous. Add in the fear of my “lovely friend” Mary making an early entrance or my skirt becoming propelled sky-high by a strong wind uncloseting my Victoria’s Secret obsession, I just couldn’t find the courage to do such an enviable act: go into the world without underwear. I would much rather have panty lines, which, on a number of occasions, I did.

The day I took the plunge and walked the streets sans my VS cotton security was new and quite different, but in a lot of ways it had a familiarity to it that had come to define my travels.

It was the morning of our final full day in Puerto Rico when I decided that “today was going to be the day.” I was going to go uninhibited into the world, literally. The tiny island had no idea what it was in for. I carefully selected the outfit that would mark the momentous occasion: a fitted, knee-length, cotton/spandex dress that I had purchased from French Connection a few years earlier but had worn only twice. On both occasions, I was quite uncomfortable with the bra and panty lines that were so easily visible, plus the sheerness of the dress let anyone who cared to know that I was quite fond of pink, bikini briefs. No matter my discomfort, I stuck to my guns each time I put the dress on, but after time 2 I decided to forgo wearing the dress altogether until I got up the nerve to do what I knew needed to be done.

That morning as I prepared for another sunny day traipsing the small, but crowded streets of Old San Juan, the nerve hit. I wanted to wear that dress, and I wanted to wear it right, which meant no underwear. My beautifully done bikini wax the week before had made me physically ready and, although nervous, my shoot, I’m on vacation, attitude had put me in the right frame of mind to get it done.

Walking around that day, eating a great brunch then bouncing in and out of the small shops looking for the perfect souvenirs to remember my trip by, I felt so sexy and free, giggling to myself about my little secret. Feeling ultra womanly as the wind made its way to my uncovered unmentionables. While this would have been no big deal for other ladies, for me, it was special and signified just one more time that I gave myself permission to step across the line.

This is what I love so much about travelling and taking a break from my everyday norms and rituals. Travelling and exploring new places gives me an opportunity to experience something different and to expand my thinking, to challenge my beliefs, and to try at least this one time. It’s my permission slip to push the limits of the comfort zones that I have constructed for myself. Travelling has become my excuse to just do it.

During my first trip to Paris, it was a small dish of escargot that pushed me outside of my comfort zone, in the lush forests of the Luquillo Mountains’ foothills it was zip lining on a close to 1000ft line, and in Italy it was a bike ride through Florence with beautiful hillsides and vineyards on one side and speeding cars on the other – this after a probably decades long hiatus from my childhood days of riding my bike through the neighborhood.

I’ve come to find that travelling is all about experiences and what better experience is there than to do something you’ve never done before? Each time that I’ve opened myself up to a boundary-pushing experience, it has not only allowed me to learn something new about myself but it has also given me a glimpse into my inner strength and courage. Here’s to going commando!

What is the craziest, boundary pushing thing you’ve done while traveling?

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  • Craig

    Hi there. I love your story! I too tried it, and still do it. I started shaving my body, all of it. Underwear seemed to caused chafing and irritation, so I decided to forego them. What an amazing feeling! I started it different than a most people in that, I started doing it at work. Now, I do it all the time. I can’t stand the feel of underwear. I even went commando to a job interview, in dress slacks. Do you still do it from time to time?

    • Hi fellow commando-ian! Thank you for taking the time to comment. Yes, I definitely still do it although I’m still not that comfortable with it. But I will keep practicing!