holy-cow.se : My Coming Out

Coming out of the cocoon–Planning and Day One

For many crossdressers like myself, the desire to go out dressed in public is very often heavily outweighed by the fear of going out in public. This is my story of overcoming that fear, and coming out of the cocoon. This happened three years ago (October, 2016), and since then, I’ve been out over 100 times.

Prior to the events I describe here (and in three more installments), I had been out only a couple of times; the prior two years (2014 and 2015) on Halloween, and the prior year (2015) for 1 1/2 days in San Francisco (went to Reno for a guys golf outing, and made a side trip to SF to have some girl fun; my suitcase was half golf stuff and half girl stuff, with the girl stuff on the zippered hidden side).

This was going to be my full immersion into dressing. My wife was out of town from Monday afternoon to Thursday evening. That meant I had three days to let my other half out. I planned this for a couple of months. I’m anal; I like to plan stuff so I’m not as nervous as just winging it.

I had four items on my “bucket list”.
1. A manicure (Monday);

2. A makeover at Sephora (Tuesday);

3. Trying on dresses at Nordstrom (also Tuesday);

and 4. Buying a wig while dressed (Wednesday).

The Thursday before all of this was going to happen, I ran an errand for my boy side. That was my cover story to visit the St. Louis Galleria, home of Sephora and Nordstrom. I wanted to determine the closest entrance in the parking garage to Sephora.

I finally worked up the courage to walk into Sephora and set the appointment (by setting an appointment, I wouldn’t get cold feet and chicken out). I talked to a SA (a guy, by the by) and I asked if they did guys and he said yes (I knew the answer; I just wanted to hear it in person), and he helped me set up the appointment (2:30 PM, when hopefully there were a few less people for the walk in from the parking lot–the idea of walking in, in woman’s clothes, but without makeup, didn’t thrill me–but at least I determined it wasn’t too far from the car to Sephora).

After setting the Sephora appontment, I walked to Nordstrom. I was wandering around and a SA (Diamond) walked up to me. I screwed up my courage (I almost backed out) and told her about the Sephora appointment, and asked if I could come afterwards and try on some dresses. She said she would check with her manager, and a little bit later she said it would be fine. She gave me her card with her email and phone number and took my first name and cell number.

I was nervous, but happy I had followed through with my plan. Clearing things with both places made me a little less anxious, and more “pot committed” (in poker lingo) to actually carry through with my plans. Afterward I sent Diamond an email from my alternative email address, thanking her for her time, and telling her when I planned to be there.

Monday finally arrived (I was like a kid waiting for Christmas to come), but before my appointment for my manicure, I had an appointment to donate platelets at the Red Cross, and then to get my nails done at 4:30.

While donating platelets (somewhat like donating blood, but you have two tubes hooked up, one in each arm), Diamond, the Nordstrom SA, called me, asking whether I wanted long or short dresses, formal or not. As I had people donating on either side of me, and not wishing to out myself to strangers over the phone, I didn’t go into much detail, but said yes to all. She said she would pull some dresses for me (my god, this is really happening!).

My manicure was set for 4:30 at a local Beauty Brands (wife leaves at 3 PM, get nails done at 4:30; am I ready or what?). If I got my nails done, I wouldn’t back out on the Sephora or Nordstrom arrangements.

I went in boy mode. I had a very friendly nail tech, Cailie, and she asked what I wanted, and I told her about my plans, and how I wanted girly nails. We talked about a wide range of subjects while she did my nails. We then walked to another area to pick a color, and I wanted it to be red. She picked a couple and we went back to her station (which was out in the open). She tried both on my fingers, and asked what I was going to be wearing. I pulled my phone out and showed her a picture of the outfit I planned to wear. She said she liked my shoes, and we went with the darker red. She painted them, and told me it would take about 45 minutes to dry. I had a few logistical issues. I had my wallet in my pocket, as well as my car keys. Cailee pulled them out, I paid, and tipped her, and went to my car and played Sudoku on my phone for about a half hour until I thought they were dry, and drove home.

After dinner, with new painted nails, and recently shaved legs, arms, and chest, I decided to get dressed (naturally). I get done at 8:15 and had the urge to get out, but where? The local mall was closing at 9, so that was kind of out. I called Beauty Brands, asked if Cailie was still there (she was), and jumped in the car and drove to Beauty Brands.

Cailie was with a customer so I looked around and talked with another SA for about 15 minutes until she was done. Cailee came out, picked out the nail polish for me to buy (gotta paint my toes now with the same color), and I also brought a brush. Cailee took my picture and we took a selfie. She said I looked good, and liked my top, and she and the other SA were jealous about my day at Sephora and the Galleria. Both were really supportive of my dressing.

I told them I might be back in the spring (my wife will be out of town again), and the next time I came to get my nails done I would be in girl mode. The other SA approved (note: I did make it back in six months, but that is a story for another day).

It was a good start. More to come….