To Mexico and Back Again (Cruise part 1)
- Kendra Chelsea
- Jul 17, 2016
- 3 min read
I cannot begin to explain how I felt being myself, for any length of time, as myself. And even though I had brought some men’s clothes with me on our ten day vacation, I had no intention in taking them with me on the cruise. They were there ONLY for the part of my vacation when I spent some time with my brother.
So my first mistake was driving to Tampa straight through the night arriving just in time to board the ship. Second mistake was trying to take a nap before we got under way; I had forgotten that they always have a safety briefing just before the cruise departed.
I was tired, frustrated and was in a rush to take a shower and get ready to meet up with the other transgender passengers. Still, even though I was in a bad mood I was actually pretty anxious to meet other people that were like me, different.
This vacation would actually have me bond with my mother-in-law. I loved her crassness; her temper and brutal honesty as in, “I think I saw some of “your people” in the lobby. Trust me, I gave it back to her in spades. The family decided an ongoing prank for her. All of us, constantly asked “Are you okay Mary? You look sick.” There were times we even had complete strangers as her too.
It only took 2 days before she threatened to kill me in her sleep. Trust me, she’s an angry sweetheart.
I was in such a hurry to meet up with my group it showed in the way I treated my family. I was snappy, grumpy and sometimes pouty and in retrospect it should have been the best time of my life. Stephanie, the cruise director was nice and welcoming and the others had a great story to tell.
There was one however, that was strange and creepy. To be honest, I think he came in hopes of getting lucky with one of the other people. At best he threw on a long wig, no makeup and short, shorts and constantly talked about sex and after we had all met up he spent the next several hours stalking us from a distance.
That first day on the ship was a little disheartening. I am not sure why but I expected a little more, maybe I was looking for a friend a little too hard, maybe I came off a little too desperate. After dinner the only plans I had to meet up with the rest of the group was to help Stephanie pick up some hormones once we got to Mexico.
That night, however, was just amazing. Miranda, Brendan and I hung out at the club at the top of the ship dancing, drinking and having a blast. We met up with a gay men’s group there that was my first experience with answering stranger’s questions.
I had always thought that gay men and transgender women do not get along; I couldn’t have been more wrong; we talked until daybreak. Once I finally decided to call it a night (because we had plans to do a shore excursion in Key West) one of those gay men followed me to my room and giving me a kiss good night.
By the end of the cruise my family was sort of well-known on the boat. Just about everywhere we went someone would call out our name and waive even though in most cases we had no idea who they were. I think it was because we were with the late night party crew.
I felt obligated to meet up with the other transgender people on the last night. Besides my son had a bit of a crush on a girl with the group, no she was not transgender, her father was a transgender man and she had went on the cruise with him.
Even so, it was just as I had imagined it would be. (Based on earlier encounters) Girls talking about how difficult things are, how bad their life is, so I let my family hit the casino while I hung out with the group.
And just when you think things are not going to go your way, they do. One of young transgender men started talking to me, I would say he was the best looking guy on the ship, the bad news was it was the father of the girl my son had a crush on.

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