A Strange Thing happened on the Way to Macy’s

The following anecdote I am going to share is something that has me somewhat puzzled, and serves to better illustrate the sometimes chaotic mindset of the crossdressing male. I consider myself a proud crossdresser, but I was surprised by my reactions.

You want me to tell you the actual story, you say? Of course!

My girlfriend and I needed to visit the Clinique counter at a department store. She needed moisturizer and I needed a refill on my foundation. Macy’s was the closest place to get to at the neighborhood mall. So off we went.

I had no problem joking with the Clinique technician as my girlfriend asked her for advice on what best to purchase. Once my girlfriend was content with her choices, I asked the technician for a refill on my foundation “for me”.  Both my girlfriend and me were relaxed and worry-free when it came to interacting with the Clinique staff. Maybe it was because I had positive experiences previously at Clinique concerning makeup and Savannah that instantly put me at ease. Let it be known that I was not dressed at Savannah that day.

Next was a quick look around in the Women’s department to look at a dress or outfit to wear to an upcoming Transgender Day of Remembrance event where I would be speaking in from of a crowd. As always, nothing I currently owned seemed appropriate enough for the occasion. We looked around and found some very nice apparel, but too expensive.  So off we went to the clearance section of the department, where we found two beautiful wraps that would complement an outfit I already owned perfectly. In order to make sure that the wrap would fit around my shoulders, I had to try it on. My girlfriend was fearless as she slipped my arms into the sleeve and had me turn around (between the clearance racks) to see how it looked.

While my girlfriend was fearless, I was not. I was nervous, worrying about what the other bargain shoppers were thinking about this man trying on a woman’s long sleeve lace wrap. I was worried about their judgment even though I would never see them again after this department store visit. My girlfriend was nonchalant with what we were doing, while I was preoccupied with other people’s impressions instead of focusing on the wonderful moment my and girlfriend and I were having.

A shared experience for our feminine selves.

A partner’s understanding and support.


How can I preach confidence and pride for our authentic selves when I cowered under the weight of what a casual observer may have thought about me? Maybe, I would have had more confidence if I had been dressed as Savannah. It is hard to say. What I can say is that I recognize that I still have a long road to travel for understanding and accepting myself. As always, we are works in progress, not perfection.

Author: livingwithcrossdressing

I am many things. I am a life-long male-to-female crossdresser and author. I hope my journey is of value for those who may need help to foster, support, and understand who they feel themselves to be.

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