Oh Brother; I am a Coward
- Kendra Chelsea
- Jul 21, 2016
- 3 min read
When I had made all the plans for the cruise, several months prior, I had promised Kimberly that once the cruise was over and, while we were still in Florida, I would be a man for her again. I really did not understand at the time how important my life change was to me when I made the promise.
Still, I bucked up. Once we got to the hotel, with much trepidation, I put away my girl clothes and became Ken again. Still, it was a very difficult time for me.
Kimberly calls me a fun Nazi as in I plan every second of our vacation all the way down to free time rest and naps. So as per our schedule, we checked in the hotel, took a very quick nap and we were off to the outlets for some quick shopping.
I actually found it quite odd that being out like Ken again after being dressed like Kendra (everywhere but work) I felt very self-conscious, like everyone was looking at me. I know it’s crazy but I felt like I was being clocked as a transgender man.
Anyway, the next two days, even though I was having a blast and really started bonding with my mother-in-law, had me feeling dreary and not myself. It was our final day in Florida and we were supposed to meet up with my brother Bryan, his daughter Amber and son Corey for a day at Universal Studios.
I had mentioned getting two tattoos to my brother, one on my back and one on my calf and ankle. I think I had plans to show him and finally come clean and tell him I was trans. However, after showing him the cherry blossom and butterfly on my ankle his over-the-top response about being gay made me deny even having a second tattoo. (Because the tattoo said Kendra on my shoulder blade.)
Look, I love my brother, but he can be vicious. Yeah, yeah, Brendan must have said this a thousand times. “If I were transgender, I would tell my brother.” I wanted to, really I did. The thing is, he was going through a divorce at the time and I spent the day with him knowing he really did not like women that particular day. Pair that with his comment, “No one likes a fat chick.” (Directed at me and my gay tattoo) I decided to take a pass on baring my soul to him.
Still, while at Universal I received a call from Paul telling me he would love to bring Samantha down for a visit (all the way from Ohio) the following weekend. Of course I welcomed him and told him I would show him around D.C.
After I talked to him I think my head went into the clouds. “Yeah, I could see myself dating him, he is really cute.” I thought to myself. “He could be my first boyfriend after beginning to transition.”
“What are you all goo-goo eyed for?” Kim asked as we got on the Harry Potter ride.”
“I will tell you later, promise.” I responded.
So yes, I had a great time in Florida with my family; yes I felt uneasy being Ken, but heck I did it for work every single day.
Even so, I really was disappointed in myself for not telling Bryan. Brendan was right, he is my brother and he had a right to know. I would soon find out that it would not be the last time I disappointed myself in that regard.
As soon as the day was over and we started to pack for our return trip home, I slipped on a nightgown and finally felt like myself again.
It would be on that same 14 hour car ride that I would do a lot of self-reflection and after 6 months of living as Kendra come to some startling revelations, especially since it was the first time I started noticing the effects of hormone replacement therapy…My breasts hurt like a bitch.

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