Here is my story. My name is Jenna. I’m in my 40’s and grew up and lived most of my life in Northern CA. I’ve been living in Honolulu for the last 3 years. I was raised in a large, close, loving, yet conservative family. I didn’t know a single person in my circle of friends or family that identified as LGBTQ.
I was raised alpha male (athletic/masculine), all the while, having curiosity or thoughts of being female from a young age. I first remember trying on my mothers and grandmother’s clothes and makeup around 4 or 5 years old. I remember every time I would, I felt a sense of excitement, gratification, and further curiosity.
In grade school, I would often fantasize about being one of girls on the playground curious to what it would be like to wear dresses to school and have friends that were girls as one of the girls myself. I seemed to be drawn towards and relate more with girls. For this reason, I was a very quiet and reserved kid.
I grew up athletic and was one of the better athletes in most sports among the other boys. With that said, this alone, may have served as a conflict to how I felt inside. Even though I was quiet and maybe a little socially awkward, being an athlete helped me make lots of friends and have several girlfriends as I wasn’t a bad looking kid.
When I hung out with my girlfriends, I think I was more fascinated with their way of being than I was to them as girlfriends. I liked both but I always wanted to be a girl myself. I loved the way they dressed (dresses, nylons, hair, make up etc.) I also loved the fact that girls can do the things boys can do without being judged (at least not to the extent a boy would be judged if they wanted to do girly things). Since I was an athlete I wanted to be one of those athletic girls. These thoughts at that time were only thoughts.
I didn’t know what transgender was. I’ve seen cross dressers on TV (movies/talk shows etc.), but it seemed they were always the headline of a joke or looked at as funny or weird. I would sometimes dress up at home when my parents were gone, for Halloween, or dress up days in high school. Total times I dressed up growing up was probably less than 15 times. It wasn’t very often, but I sure thought about it a lot.
Ironically, I joined the Marine Corp after high school. While I was in the Marines, I shaved my body for the first time (legs, arms, under arms, chest etc.). I’ve kept my body shaved ever since. Overall, I just prefer not to have body hair, but mostly it’s my way of feeling feminine without dressing. I learned not to care if people comment on my shaved body. Many athletes in certain sports shaved their entire bodies. A few other Marines did as well, but probably for different reasons (swimming, muscle definition etc.)
Out of the other Marines, I was considered one of the toughest. Boxing has been a hobby of mine and I can definitely hold my own. I also played baseball in college. But even after all the masculine stuff in my life, gender dysphoria has always existed.
I married my high school girlfriend and talked with her about this after high school. She was very open minded and supportive. We started dating at 15 and married at 20 and unfortunately divorced at 27 as we grew apart. I cross dressed at home on occasion with her support in my early 20’s.
I had a relationship with a girl after my marriage ended who I also opened up to about this and she too was also supportive. The first time walking out of the house dressed was during that relationship in 2005. We went for a drive and looked at Christmas lights. I went for a drive one other time by myself shortly after. Even though she never showed intolerance, I have a hunch my crossdressing/dysphoria may have played a part in our break up after 2 years.
I remarried shortly after to someone I never told about my thrill of cross dressing. I suppressed my thrill and purged everything for the next 2 years. Maybe I was looking to start over without coming out and pretend it didn’t exist… I don’t know. That relationship only lasted 2 years, ending in 2008.
Over the next 12 years I’ve had 6 relationships having told all but 2 women about my cross dressing. All have been supportive and have ended for different reasons. The 3 relationships I didn’t tell, I felt wouldn’t have accepted it.
During the time period of 2015 through 2016, I was single and alone and forced myself to explore my crossdressing and gender dysphoria further. I sought counseling and ventured out in public for the first time. My first time was at a private social group where I was able to get dressed at the hotel where the gathering was held. I went to 3 of those events.
My first time dressed mainstream was by myself at the local mall. For a 6 month period, I was going anywhere and everywhere by myself while dressed (mall, LGTBQ night clubs, out to dinner, drive throughs, cd/trans socials, counseling appointments etc.). I still never had the courage to pursue this lifestyle further or permanently.
At the end of 2016, I found myself 40, single with no kids and totally miserable with my career. I left a 22 year career, sold my house and vehicle, became a scuba instructor and boat captain and moved to the Caribbean. Hello extreme! My family thought I was crazy! Best decision I’ve made so far. Other than being female, I have passion for boating. Of course that meant suppressing everything again for 2 more years.
I relocated to Hawaii beginning on 2018 with the intent to explore everything further again, however, this time I actually enjoy what I’m doing in my male life, which makes everything even more confusing. I met someone here who is fully supportive of my cross dressing. It’s hard to go back and forth as a scuba instructor and boat captain so things are on hold again. I’m living a pretty masculine male life and suppressing my female side. What does it all mean? I’m still not sure. Or maybe I am, but too afraid of the consequences.
I have a large conservative family who would definitely judge me and most of my friends are conservative. I’ve read many coming out stories with both positive and negative outcomes. Some will accept and some won’t. I guess I’m not quite ready to find out. I recently told my mother but kept it very brief. She didn’t flinch on it and seemed OK with it but didn’t ask questions so I dropped it.
My most recent exploration success story was in early 2020. I starting venturing out as Jenna, gaining more confidence every time I left the house. I started counseling and HRT. I flew back to CA while dressed, rented a car, used the restroom, checked into a hotel, went out for dinner/cocktails, went shopping, flew back, all with no issues.
I wouldn’t say I’m passable, but I try to look respectable and dress my age and for the occasion. I might get a few looks or snickers if people figure me out. But it seems that 90% of people could care less as most have their own lives to live. I gather that the few who pay attention and cause problems are folks that don’t have much going on and feel better when they interfere in someone else’s life (insecure, bigoted, uneducated people).
When I got back in February, I landed a full time job in the women’s department at Bloomingdales. It was the most exhilarating experience of my life! The job itself was a little too slow paced for me, but it gave me the chance to dress up and live every day as Jenna for a month. I left partially because it was boring, but I think I just got cold feet. HRT was starting to kick in and at that point I wasn’t ready. I was a little off put as the department manager kept referring to me as sir until I politely corrected him in an email. Everyone else treated me like any other woman (store manager, HR manager, other male or female clerks). I have management experience. My thought was to work my way up and get a 2nd retirement out of it. After 1 month I unfortunately left and stopped HRT and counseling. Then COVID happened and resources and opportunities are even less obtainable.
I’m back to living my life as my male self still wondering if or when I will pursue my life as Jenna again. My girlfriend and I moved into a new place that isn’t as private as the previous place so I’m not comfortable now leaving the house while dressed. If I decide to continue with transition that won’t matter. For now, everything seems to be starting over. What to do? Making like-minded friends might help! :)…
Please take the time to comment on my article or answer one or more of the following questions:
- Were you a really good athlete in either high school or college while you were enjoying privately your thrill of cross dressing?
- Were you ever a member of the Armed Services and cross dressing while in the service of our country?
- Have you ever had a full time job where you were able to go into work totally dressed en femme? If so, how did your boss or coworkers treat you?
Thanks for reading my article and possible sending in a response to the article or one of my questions.