Going Places

By Paula Gaikowski

We all start out furtively, drawn to our mother’s or sister’s closet, out of wonder and intrigue, and then one day, curiosity blossoms into bliss and we are changed forever. So begins our journey and at first, we experiment alone hidden away trying on lingerie, dresses, hosiery, shoes and makeup. As we evolve, we seek validation of our feminine visage. Eventually there comes a need to be out in the world as a woman, to be seen, accepted and validated. Those first steps are the most difficult, standing in front of the hotel room door and finding the courage to step out. I remember it well frozen with fear but still wanting to do it so badly.

How did I start going out in public? I have been asked that question often over the years and I’d like to share some of the tips and advice that made it fun and fulfilling for me.

My ventures out into the world were mostly from hotel rooms on business trips or from my home when the family was out for the day or away on vacation. So I recommend finding a base you can operate from whether it’s a hotel or home, you need a place where you can spend time getting ready to go out. This is a magical time while you transform yourself and the caterpillar turns into a butterfly, so it’s important that you can focus and enjoy the process.

It’s very important for me when out and about to be seen or even pass as a woman. However, I also love to wear feminine and stylish clothing. That being skirts, dresses, pantyhose and heels. Whereas most women wear slacks, capris or jeans. I like to use the maxim “to dress one level up.” If the ladies are generally dressed in jeans at the venue you are going, then wear slacks and a nice top. If they are dressed for the office in slacks and nice tops, then I’d try my skirts and fitted suits. You want to look nice without looking out of place. 

The winter season with sweaters and layers were always my friend and that is why a lot of my adventures were during the colder months. I could write a book about getting dressed and looking just right, but that’s part of your journey and you need to work at it and progress. That girlfriend is where the joy is in all of this.

If you’re standing in front of the mirror and she stares back at you, it’s time to go. But where? Here are some of the places I’ve had success at while growing my image and confidence.

The first steps I took out were from the hotel room to the car and then back to the hotel room under the cover of darkness. A great way to start, then I’d walk around the outside of the hotel, maybe passing a person or two. I’d go to the vending machine and buy a soda. I soon found some self-confidence and the fear subsided. 

Then one day, I left my room key in the room – dressed as a woman, I was locked outside. It was probably one of the best things that happened to me. This had been a nightmare of mine, but when it happened, I was remarkably calm knowing there was only one way to solve my dilemma, going to the front desk, showing my ID and getting a new key. Dressed in a black skirt suit, I approached the desk knowing I was crossing a threshold moment and was surprisingly composed. 

“Hi, I can’t believe it, but I seemed to have left my key in the room.”

Without missing a beat and with a smile, she asked for my ID. All this time I’m wondering does she realize that I’m a crossdresser? Is she going to gasp when she sees my ID? 

A professional, she smiled and handed me a new key and added, “I love that pin you’re wearing.” 

I thanked her and opened an honest conversation about my predicament. She was helpful and kind and I realized at that point I was going to be able to go out in the world and enjoy being a woman. After this, I would sometimes lock myself out on purpose just so I could have conversations and interaction with someone. Keep in mind, the persons at the front desk are typically young women who are very accepting and eager to help.

My next steps out into the world were shopping malls. At first, I’d just enter, walk the length of mall stopping along the way to look into the windows of different shops and use the reflection to notice if people were noticing me. They weren’t – they just walked by busy with their own lives. Eventually, I started going into different shops (my favorites were Nordstroms and Lord & Taylor). I was always treated as a lady, used the fittings rooms and bought dresses.

Another early destination in your voyage should be to a transgender boutique such as Glamour Boutique, Rori’s or Janet’s Place. Here you can show up en femme and be sure to find a supportive environment. My first makeover at the Glamour Boutique in the 1999 was life-changing.

Cosmetic counters are supportive and helpful to transgender women. After you’ve made your first few walkabouts, make an appointment for either a makeover or makeup lesson at MAC, Sephora or Ulta. Give them a call and tell them you are transgender and want a makeover. At Mac, a 60-minute full makeover in a private room is $60 and a 90-minute lesson is $90. You can expect a bubbly and expert makeup artist who is excited to help you. 

I started doing this in almost every city where I had a business trip. I’ve lost count on how many makeovers I’ve had, but I learned so much about makeup, cosmetics and femininity. This is a great next step in your journey.

Another safe and fun place are busy office parks. I’d find a busy office complex and walk through the lobby, stop and have a cup of coffee in the café and just stroll around and be seen. It’s just a great way to get out and build confidence.

Wig stores also count on the transgender community for a share of their business. Give them a call and make an appointment. If you are in New England, I recommend Amanda Thomas wigs in Nashua, New Hampshire. They are a great friend of the community.

I spent about five years going to a therapist – it was a great decision. I told my wife it was for depression and stress and she was on board 100%. Going to a therapist was one of the best things I could have done. Being able to talk about “anything” was so cathartic and healing. 

I never expected to go to a session dressed as a woman. When my wife and daughter were on vacation, I woke up on the morning of my appointment and got all dolled up and said, “What the heck!” and drove into Boston. I parked the car and strolled through the campus of Boston University Medical center in a business suit, had breakfast in the café, rode the elevator with a Boston cop and l use the ladies’ room. Then I met with Dr. D who smiled a mile wide when he saw me. A great break through and awesome session. I can only say if you are looking for a safe space to go out as a woman, your therapist is the place.

Going out with other girls or attending a support group meeting is another great way to meet others like you, learn from their experience and express your feminine side. I had the chance to attend a transgender conference when my business trip and the Colorado Gold Rush conference intersected. It’s an amazing experience to meet scores of other just like you. I’ve also made connections thru social media with other transgender women and met up with them while traveling. I’ve attended a support group meeting in Chicago, went to a concert in the UK and visited the Ronald Reagan Library.

Dining out by myself after a makeover or shopping in the mall was always fun. I always liked Cheesecake Factory where I’ve always been treated well as a lady.

I still have a few other events on my bucket list. I’d love to attend a wedding en femme or even be a bridesmaid. 

I’ve never flown as a woman and I know that many do. When on business, I would always envy all the businesswomen in the airports and always wished I could be like them. I’d love to fly somewhere as a woman with only my girl clothes and attend a class or conference as a woman for a whole week. 

It’s important to remember this is a joyful and delightful experience. Ask any sister who has spent time out in the world and they will tell you that the fears they had about going out were unfounded. Enjoy all the little successes, learn from the stumbles and remember, you are doing nothing wrong – it’s okay to be transgender, so let her loose and be free.

Wearing Nine West

Another modern couple (boy and girl)