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To Mexico and Back Again (Cruise part 2)

  • Kendra Chelsea
  • Jul 19, 2016
  • 3 min read

I really didn’t want the cruise to end for a couple of reasons. First, I just felt so welcome and wanted, I learned so much from both the transgender group I was with and the gay men’s group that I ended up hanging out with. Second it meant the second part of my vacation would begin, seeing my brother and for the first time in many months, looking like Ken and not Kendra.

But it was the last night of the cruise that really stuck with me; as I mentioned Brendan had a crush on this girl and I had the opportunity to talk with her father in the upstairs club. I have to say he was an amazing transgender man. He was a little shorter than me but you could tell he worked out, very cute.

But it was when he said I was pretty, well my head started spinning a bit. The thing is, it was spinning more at the fact my son had a crush on his daughter. I must have looked strange when I said, “Hold on a sec, I will be right back.” And rushed downstairs to the casino.

I found Brendan right away, he was with Kimberly, her mother and Miranda. “He, I hope you don’t think this is weird but would you mind if I flirted with Paul, I know you are interested in Samantha and I didn’t want things to get strange.” I mumbled, obviously a little befuddled.

“Sure why not Kendra.” Brendan replied, not looking up from the roulette table. “It’s fine.”

Well see, I knew he wasn’t close attention to what I said and I wanted to make sure he had a clear picture of what I was trying to paint. “Okay, let’s say you ended up dating Samantha, and I end up dating Paul, don’t you think that could get a little odd? I mean take it to the extreme, what if I married Paul and you married Samantha, I would be both your Dad and Mom, Stepdad and Step mom, oh man, there is so much wrong with that thought.” “I getcha…No it’s fine. I am seeing Samantha at the hot tub in about an hour, it’s cool really. I think Paul will be there too.”

Still, I was a little surprised by his laid back attitude, even with what I thought of as some “new age” bullshit but decided not to argue with him. Instead I headed back to the club to see Paul.

And of course, odd ball Kendra had to run off in the middle of a conversation because of that he had left the bar. Sure I had a great time. I loved all the gay men I got to hang out with, loved how one kissed me after we partied together but it wasn’t the same. Paul knew the things I was going through and I kind of wanted to tap that knowledge but…I figured it wasn’t meant to be.

Since we were departing early in the morning, I decided to call it an early night (for the first time) so after another drink, I headed to the pool area to tell Brendan good night and see how he was fairing with his crush.

And wouldn’t you know it? I forgot all about Paul planning to be with his daughter and Brendan at the hot tub. “Hey…um…you.” Yep, I forgot his name.

“Paul.” He replied

“I know, sorry…” (Fuck did I just smile like a school girl?)

And then we talked, it was easy, not forced and then exchanged Facebook information “Just look up Kendra Chelsea…Maryland”

And then we exchanged numbers at the same time Brendan and Samantha was exchanging numbers.

At that point I didn’t want to overload them with a bunch of airheaded Kendra bullshit. “Well, we have to get up early, I am not used to getting up early so…” Yep , short doses is what they needed, I excused myself and headed back to my room, wall to wall smile. Still it was difficult getting to sleep, I had way too much running through my head.

Miranda and Kendra Chelsea before HRT

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