Tina’s Tipping Point

(and the lengthy time it took to get there)

By Tina Davis

I’m telling a bit of my history here, but I feel it’s worth the time to understand what changed in my mind about crossdressing and how I reached the decision to go out in public.

I started dressing around the age of 10, wearing my older sister’s and my mother’s things when I could. But I had a different reason for wearing them, one I will only say involved a specific kink. This drove my dressing for many years, where I never had interest in looking female from the neck up. No wig or makeup, but I would always fill out the bra with socks or pantyhose. I wanted my body to look feminine, as I would think of myself as a woman while dressing. But going out dressed was the furthest thing from my mind.

I found the courage to buy some of my own things in male mode in college and when I started living in my own apartment. Living near Boston, I discovered the existence of the Tiffany Club of New England, a support group for CD/TG/TS people. But since I did not want to go out, I did not connect with them (yet). When my wife-to-be and I decided to live together, I purged the few female clothes I had. I did try on many of her dresses and heels when she was out, as she was similar in size to me at the time, and continued even after we got married. After the birth of our daughter, she had difficulty losing the pregnancy weight and went up in sizes. I also found many of her heels didn’t fit me well, being slightly big.

I began buying my own female clothes again, just a couple of skirts and a sweater to start. Then it was panties and bras and dresses, I already had my own pantyhose. The final step was buying my first heels, which I did online. By that point in 2003, I had established Tina in an online community and joined many groups of people with similar interests. I did join the Tiffany Club’s email list, but did not become a member of the club.

I communicated with a few people from the other groups and wrestled with whether I could get up the courage to meet someone in person. It took quite a bit before I was ready, even though I knew some of the people were trustworthy. I bought a cheap Halloween blond wig and used some of my wife’s makeup to see what I could look like. After some practice, I met another CD in male mode and agreed to another meeting en femme in April 2011. She brought me another wig, much nicer than my old one, and I saw how much better I looked with it on.

This was the first time I seriously thought about going out dressed, but I only went to the Tiffany Club, as I had no confidence in my makeup skills. Clownish puts it mildly. I didn’t get out again for two years, although I started working more with makeup and buying my own limited supply. I went back to the Tiffany Club in July 2013, feeling a little bit better about myself, but still not ready to step out into the “real” world.

It took almost another three years before I had the chance to go out again. This is where my earlier post about my 2016 adventure comes in, and is my true tipping point. I had been buying clothes in male mode and online with no issues, and I had recently joined crossdressers.com to find more people who shared my approach to dressing. With amazement, I read their stories (including Kandi’s!) of going out dressed with confidence, and I started wondering if I could get up the nerve to do the same. As I wrote in that earlier post, I went shopping in androgynous mode and had no trouble. I dressed fully for another evening at the Tiffany Club and got a makeup tutorial on bringing out my eyes. Even though I did not go out elsewhere, I felt so much better about myself and knew that the next time, I would not be so timid.

Of course, that event didn’t happen until 2017, but by then I had lost most of my fears about going out and was so happy with my days fully dressed. Getting a manicure, being called “this lady” and “her”, shopping in many stores, and visiting the Tiffany Club again were all wonderful experiences. Since then, it seems like I have to get out when I dress. My feelings have changed so much in the past decade, when I originally felt I would never go out in public, to knowing the joy and happiness I feel when I go out as Tina. I no longer feel the need to go to the Tiffany Club, but prefer to meet others in public places and just be seen as women enjoying their day. I do keep to myself or with one or two others, as I tend to avoid large groups.

It has been a long road to get to this Tipping Point, but I’ve now seen the same response that so many others have. I realize how much more fulfilling being out as Tina is then my early dressing forays, and heartily recommend taking that step out your door.