Interview with Jessa Kay

Monika: Today I would like to introduce to you Jessa Kay, an inspirational woman from California, the USA, that shares her story on social media. Jessa and I are going to talk about being trans and the challenges related to her fascinating journey towards womanhood. Hello Jessa!

Jessa: Hi Monika!!! Thank you for selecting me to interview.

Monika: Could you say a few words about yourself?

Jessa: I’m a 39-year-old transgender woman. Originally from West Virginia, currently living in Los Angeles, CA.

Monika: What inspired you to share your intimate life moments via social media?

Jessa: There was a time when I was coming to terms with my internal struggle of knowing that in my heart, mind, and soul that I was a woman. I took comfort and drew inspiration from other transgender women who were brave enough to share their journey. Now that the shoe is on the other foot, I feel it is my responsibility to share my journey with other budding transwomen who might need some comfort and inspiration.

Monika: I love your name. Why did you choose it?

Jessa: There are similar elements to my dead name. Some trans folk try to get as far away from their dead name as possible. For me, starting at 35, it was easier and more comfortable for me to pick something similar. Also, I loved the character, Jessa, from the show Girls on HBO. It came down to Jessa or Jemma and Jessa just felt right.

Monika: Do you get many questions from your followers? What do they ask for?

Jessa: I do! It’s mostly just transitioning advice from my transgender or trans-questioning followers. I’ve answered questions about surgeries and what to expect from hormones. Then of course you have the chasers and dudes that contact you on a daily basis for different reasons. That can be overwhelming but if you are gonna be a transgirl on the internet it’s gonna happen.

"I took comfort and drew inspiration from other transgender
women who were brave enough to share their journey."

Monika: We all pay the highest price for the fulfillment of our dreams to be ourselves. As a result, we lose our families, friends, jobs, and social positions. Did you pay such a high price as well? What was the hardest thing about your coming out?

Jessa: I was employed by a law firm for 4 years. I really liked that job and probably would have stayed but it was a mostly white, straight, cisgender conservative work environment. I stayed until I could no longer physically hide it. I wasn’t fired but they definitely would have found a reason to fire me had I come out. Coming out to my family was the hardest thing. It wasn’t great at first. We are in a pretty good spot now but it is continually a work in progress.

Monika: Are you satisfied with the effects of the hormone treatment?

Jessa: I was satisfied with what HRT did for me. I gave it two years before surgical intervention. I started at 35 so I am lucky that I had the effects that I did.

Monika: We are said to be prisoners of passing or non-passing syndrome. Although cosmetic surgeries help to overcome it, we will always be judged accordingly. How can we cope with this?

Jessa: Therapy lol. I think that we have to try to remember to set realistic goals. Of course, I want to be that beautiful, perfect, petite dream girl model. But a lot of women want that whether they are transgender or cisgender. It’s all societal. But I have to remember that I was born and lived in a male body for 35 years. There is only so much you can do and you just have to take stock and be thankful that we can accomplish the things we can with modern science. I really envy the transgender youth of today that can be aware of gender identity and have the ability to choose at such an early age before hormones interfere.

Monika: Are there any transgender role models that you follow or followed?

Jessa: Not really. I’m glad that there are famous transgender individuals out there who have brought it to the mainstream consciousness but I don’t really draw inspiration from them personally.

"Coming out to my family was the hardest thing."

Monika: Do you remember the first time when you saw a transgender woman on TV or met anyone transgender in person?

Jessa: The first time I saw a transwoman at all was a girl I randomly saw on Myspace (showing my age lol). She was a mutual friend of a close friend of mine and I was obsessed. So jealous of her but I was also so intrigued by the fact that it was a possibility.

Monika: What do you think about the present situation of transgender women in your country?

Jessa: I believe that it's the best it has been for transwomen in America but that is a pretty low bar. I'm still stared at, called awful names, and still have a stigma attached to my identity and state of being. Transwomen of color are the ones who are really going through it. The murder rate for black transwomen especially is just incredibly sad and something HAS to be done. It's hard to be trans but I can't even imagine how hard it is to be a black transwoman. BLACK TRANS LIVES MATTER.

Monika: Do you like fashion? What kind of outfits do you usually wear? Any special fashion designs, colors, or trends?

Jessa: I love fashion. I'm a dress girl. I wear dresses every single day! My mom and aunt tried to tell me I needed to wear other things and I said "I couldn't wear dresses for 35 years so I'm making up for lost time" 

Monika: Do you often experiment with your makeup?

Jessa: I did a lot more when I started. Then I fell into the simple everyday makeup routine just to make my life easier. I still love to play with makeup sometimes though.

Monika: By the way, do you like being complimented on your looks?

Jessa: I do!! I've worked hard to get where I am so it's validating to hear compliments.

Monika: Do you remember your first job interview as a woman?

Jessa: I actually haven't had one yet. I interviewed in boy mode for Starbucks and told her in the interview and she encouraged me to come to work as myself.

"Be confident in yourself and your identity."

Monika: What would you advise to all transwomen looking for employment?

Jessa: Find somewhere with a liberal environment that has good insurance that covers gender-affirming surgeries and treatments. Most importantly, be confident in yourself and your identity. If they don't hire you because you are trans then you don't want to work there anyway.

Monika: Are you involved in the life of the local LGBTQ community?

Jessa: Not currently. I’m on the east coast seeing family for the moment. I have been thinking about visiting the center in Hollywood when I get back though!

Monika: Could you tell me about the importance of love in your life?

Jessa: As far as love goes, it depends on what type you are referencing. Family love is highly important to me. I’m straight but I have never been the type that needs a relationship. I’m more the “if it happens I’m open to it” type of girl.

Monika: Many transgender ladies write their memoirs. Have you ever thought about writing such a book yourself?

Jessa: I have been told numerous times by different people that I should so who knows? Maybe I will.

Monika: What is your next step in the present time and where do you see yourself within the next 5-7 years?

Jessa: My current step is to return to Starbucks and work there to continue the surgical part of my journey. I’m working on creating a transgender comic book/superhero with another transgirl and I would love to see that go somewhere in the next 5-7 years.

Monika: What would you recommend to all transgender women that are afraid of transition?

Jessa: Seek therapy if you haven’t yet. Talking to someone can clear things up. If the transition is the answer, you will come to it on your own terms. It’s not something you can run away from. Embrace your true self.

"Now that I am myself the sky is the limit!"

Monika: My pen friend Gina Grahame wrote to me once that we should not limit our potential because of how we were born or by what we see other transgender people doing. Our dreams should not end on an operating table; that’s where they begin. Do you agree with this?

Jessa: I do! I never dreamed that I would ever be Jessa. I thought that I was stuck. Now that I am myself the sky is the limit!

Monika: Jessa, it was a pleasure to interview you. Thanks a lot!

Jessa: Thank you!! The pleasure was mine.

All the photos: courtesy of Jessa Kay.

© 2021 - Monika Kowalska