I have struggled with self esteem issues for pretty much my entire life.
I can’t recall ever actually being happy about the way I looked as James. Thinking about it in a new perspective, I can see my gender dysphoria having a lot to do with that, if not even it being the root cause. Every time someone called me ‘handsome’ I would instantly discredit the compliment internally. I never wanted to be handsome anyway, I wanted to be cute.
My first girlfriend was at age 26. I had a lot of crushes from grade 6 until then. I spent an entire year going to the local mall as many nights as I could to hang out and talk to a particular girl that worked in a clothing store there. Even taking her lunch break with her. I never got the nerve to even ask her out. This was pretty much normal for me.
There was even one time where a girl asked me out via a note, and she was even a redhead (I’m partial to redheads) and I couldn’t call her. I was so socially awkward in that respect. I could have girls as friends – I was just unable to move beyond that. I had a hard time even thinking of what a relationship would look like, since I liked wearing girls’ clothes. Surely, I couldn’t tell them, so I’d have to hide the clothes, and then be extra sure not to say anything that would give me away.
I remember trying to compliment a girl in high school about some clothing she was wearing. I got the oddest looks from her and her friend. That immediately stopped that. It’s not that they laughed at me, but there was no real acceptance of the compliment either. It was just very very awkward.
The first girlfriend came about because she worked with a close friend, and we (all parties) wound up at this friend’s parents house for a bit and chatted briefly. Later I was told she thought I was cute. That was the key word. I wonder, now, if I would have gone through with dating her if she had said I was handsome. 🙂
No one knew I was inept and VERY inexperienced at relationships. I did tell her on our first date, that I hadn’t had any girlfriends before. She was from a religious upbringing, and was a virgin (as well) and hadn’t had many boyfriends, so it was almost an even playing field. We dated for about 3 months, and it ended poorly. Not with acrimony or anything like that, but it seemed like things were going really well – it was almost love at first sight for me. But, I think things were going too fast for her (most of you will laugh at that I think – 3 months no sex doesn’t sound very fast compared to other relationships I’ve had since this one).
She broke up with me. She had the decency to do it in person. She told me that she had had a dream the other night, and in this dream, we were getting married. At the altar she wound up running away from the wedding, and then the dream shifted. Next she was on a swing, swinging higher and higher, until she fell off and woke up as she hit the ground. This dream, I was told, was pretty much her reason for breaking up with me.
I was a mess for 2 weeks. Never having had this kind of rejection before, I was so ill prepared for it. I kept to myself while at home, worrying my roommates greatly. At work I was there but not there. My one co-worker even joked, “What’s wrong? Girlfriend break up with you?” Me, “Yep.” Him, “Oh. Sorry.”
During the 3 months of dating her, I was constantly worried about being found out. Worried that she’d see something at my place, or I’d say something wrong. I tried to figure out how to tell her, but the idea seemed pretty much preposterous. I had the feeling during the entire relationship that I wasn’t giving her all of me. This was the catalyst for me to need to tell someone.
As a crossdresser (which is how I was identifying back then) I went through what most do: purges. This is where the shame and guilt of what we’re doing builds up so much that we throw out all of our female attire and swear off dressing up ever again. I believe I did this 4 times. It’s a behaviour that I think was also involved when I got rid of my stuffed animals. It’s an effort to be what we’re not. And if my last month has proven anything, it’s that this is the stupidest thing transgender people do. (The smartest thing being accepting who we are whole heartedly)
A purge would basically involve me rounding up everything I had – pantyhose, panties, bras, blouses, skirts, dresses – putting them in garbage bags, and throwing them in the trash. A complete removal of everything. No tempting things left behind. I think the longest I went without rebuilding my collection was about a week. It’s stupid on so many levels. It’s expensive, mentally and emotionally damaging, and you always wind up letting yourself down at the end.
There was just no way to deal with that shame and guilt. It felt so good to wear the clothes, and then after you’d think about how ‘wrong’ it was to get enjoyment from that. And you’d dwell on that. Every single time. There was never once where I didn’t feel that. It’s very hard to think of yourself in a good light when you are stuck in this vicious cycle. And on top of that, having no one to talk to about it. Thinking you’re the only one that is this way (only to find out later that practically every transgender person of my generation went through the same exact thing). Then, finding shows like Donahue, and Sally, and Jerry – only to see transgender people portrayed as fetishists, or perverts, or mentally ill.
Even now, there is so little positive transgender message in mass media. There is some, and it is getting better, but there are still portrayals of transgender people being criminals in shows like CSI (which has shown transgender people in good light too).
I wound up being a virgin until I was 29. At 29 I was dating a woman who was very much into me, and I was only somewhat into her. I basically surrendered my virginity to avoid being a 30 year old virgin. Up until this point, this wasn’t something a lot of people knew about me. I never lied about it, but I would always be very vague. I don’t care to hide things anymore, or be vague. It’s not helpful.
I actually think that my losing my virginity at that point was detrimental to my self esteem. It was probably very close to date rape. It was our second date, and she had tried on the first date. Funny how I don’t even equate her wanting to have sex with me that badly as a self esteem boost. This is not a relationship that I did well in. It’s the one where I tuned out and essentially made her break up with me. So, the whole thing kind of makes me feel worse about myself.
Skip ahead to now and things are very different. It’s probably apparent to some of you or most of you, but my self esteem is miles ahead of where it was. Even if I’m not the most feminine looking woman facially (and that may [hopefully] change with hormones) I can look in the mirror and see a cute woman. I can walk with my head held high and look people in the eye when I’m out now. Before I allowed myself to be authentic, if I went out dressed as a woman, I was always looking down, trying to draw the least attention to myself. Now, I value that attention.
Yes, I get ‘read’ often, but probably not even as often as I think I do. I blend in, but I don’t do it by retreating. I do it by being confident in myself. I don’t purposefully do any specific feminine mannerisms, I let it all come out naturally. There’s a spring in my step when I walk, I smile for no reason. The rigidity of masculinity is gone, I’m way more fluid. I don’t care that I’m 6’5″, or that my hands are big, or that my feet are large. Instead, I am proud that I’m tall, and can be seen from across a crowded room. My fingers are long and slender, so while not the prettiest, they aren’t grossly masculine hands. My feet are also not that wide, and I have found wonderful boots and shoes that look good and proportional on me (as long as people don’t see my feet without socks or stockings, I’m fine lol).
There are steps to go yet in my transition that will aid my self esteem even more. And I am very much looking forward to them.
– Jess
Addendum (January 11, 2015):
Teresa pointed out that I skipped over our marriage. It wasn’t a conscious decision. I definitely had issues of poor self esteem over the last 10 years. My infertility being the biggest blow. At that time I was still identifying as a male, and it’s a pretty big hit to your view of self when you fail at being a male. That was how I viewed my infertility; a failure. Obviously it was nothing I had done, but it was part of me nonetheless.
Another thing I had issues with was loss of hair due to testosterone and DHT. It was a gradual loss, but I never realized how much it was affecting me until much later. Luckily Teresa managed to convince me to shave my head early on into our marriage. It made it bearable, but I’ve never been able to take ownership of my hair loss. It affects me to this day. I can make jokes about it, but I prefer to hide it beneath wigs, or bandanas, or hats, or even a wig cap. As long as I can’t see my scalp, it doesn’t bother me (as much).