My Personal Sweet 16 Transgender Experiences List
And how it compares to a two-year-old wish list

Earlier in my transgender writing journey I posted an article called: My Transgender Sweet Sixteen List. I wrote it to fill my emotional glass back up to half way. I was in a very dark period. I wrote a general list of the positive experiences of being transgender. Last night, sadly, I felt like I was looking at an empty emotional glass. I felt deep sadness. I wrote a long piece about it but I have chosen to not share it here. Who needs to be depressed further with someone else’s pain? I have done enough of it here and we all have enough in our own lives.
Instead, I thought I would share my personal Sweet 16 Transgender Experiences List. These are my personal positive experiences since I wrote my original Sweet 16 list two years ago. The list is filled with vanity and things that give me a sense of female gender validity. Please don’t criticize me if they seem superficial to you. This is all new to me and while I am learning about all the negatives of being a woman, I also feel so many joys in my personal female discoveries. I just wanted this to be my happy list:
1. I am still alive and suicide is no longer an option.
2. My family is still with me but we have a long way to go.
3. I finally accept that I am transgender.
4. I have been on HRT for two and half years.
5. I have a 38DD chest from the hormones and I am not binding my chest any more. Happily it is one more surgery I can skip and it provides me with a huge validation as I continue my journey in stealth.
6. I have been called pretty and gorgeous without me getting upset*
7. I have developed a passion for red wine and chocolates
8. I have a hairdresser who knows that I am transgender and treats me totally like a woman.
9. I have been sexually harassed in rush hour traffic by a guy who angrily yelled “Nice tits!” thinking he was insulting a guy when, in fact, he was the first one to notice I had breasts. It made me smile.
10. I started a fashion Pinterest file and like the style I am developing. I have always hated men’s clothes. I am dressing more androgynously. I find women’s clothes so much more comfortable.
11. I have been increasing my vocal range so that I can reach the high levels of the female range without straining.
12. I am getting better at makeup and, hey, if I make a mistake, it wipes off. No harm and all fun.
13. I have had hairy legs and arm pits all my life. I have very little body hair now and love shaving that bit off. The sensation is wonderful
14. I have amazingly soft skin. It is so obvious when I touch it. It makes me smile.
15. Some of my male pants are not fitting and my hips are filling out. People have noticed a difference in the way I walk and I didn’t do anything on purpose.
16. I need to stay stealth for the rest of the year but I am no longer afraid of who I am.
*For over a year, each time I did a makeover, I had photos taken of me as Emma. I had a very hard time accepting that I actually looked like that. I was massively uncomfortable with being called “pretty” and even “gorgeous”. It even made me extremely angry. It took a year in therapy to finally accept that I could be pretty.
I did the first make over to prove I couldn’t pass, epic fail! I did it the second time to prove that the first time was just a camera fluke, wrong! I went the third time to really prove I was a guy in drag and I was still hoping for a “cure” to my gender dysphoria. My denial wall collapsed. I saw in each photo a smile of deep, personal joy that I know was my heart touching my soul for the first time and really seeing it with my eyes in the photos. I have done ten more makeovers during which I walked and shopped as Emma without fear. The smile appears every time.



This is the original list that I wrote two years ago.
I was challenged by someone after writing the Transgender Pain, to write something positive about being transgender. Here’s my attempt:
My Transgender Sweet Sixteen
We get to:
1) really know ourselves in a way few people do
2) find out who loves us no matter what
3) find out who our real friends are
4) get to meet new friends
5) have new social experiences
6) understand both sides of gender
7) see the world in way that few people experience
8 ) see sex in a different way
9) try on new clothes and fashions
10) use some bathroom somewhere
11) understand people better, with more empathy
12) finally have internal peace after a lifetime of battling
13) reinvent ourselves and the adventure of getting a fresh start
14) discover exciting physical and emotional changes
15) be accepted by others and just one of the girls or one of the boys
16) feel the sheer joy every day of just being the real you
Emma Holiday
Writers note: If you have read any of my writings on Medium you will have noticed a definite theme: the incredible pain of gender dysphoria and all the difficult aspects of just being transgender.
My writing has three specific goals:
1. Writing is my therapy. I have a very limited outlet for my thoughts so I write to find a way to process the most profound experience in my life. I need to understand and I need to accept myself to move forward.
2. Being transgender, for me, is a very lonely existence and if I can share some of the things that I feel and think as I go through the process of transitioning with others who are transgender and, in some way, lessen their pain and sense of loneliness, then all of this public exposure of my personal thoughts is not a waste.
3. I write to help cisgender people understand that all trans people want is to be simply understood, accepted and treated as a normal person. We are.
Thank you for reading my work.
