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Kendra Chelsea Reviews Her Future

  • Kendra Chelsea
  • Sep 21, 2016
  • 4 min read

I glanced at my phone after I heard the notification. “Hey baby, what are your plans for the weekend?” The text read, it was from Jerry.

“Like I am going to take the time to tell him everything I am going to do.” I chuckled as I put my phone down and went back to getting dressed for my doctor’s appointment.

Seconds later I get another text. “Are you going to your therapy appointment?”

“Yep.” I replied.

“I want to see you, okay, for lunch.”

I had met Jerry just a month before; kind of funny story, two steps after I got out of the car he stopped me to tell me I was beautiful. We ended up dancing and kissing the night away at the DC 9 night club.

Even funnier story, after that first date Marcie told me…”I don’t think he knows you are transgender.”

“Huh? We kissed all night. I know I do a good job shaving but…I don’t think I am that good.” I replied.

Still, I hesitated calling him for that very reason. I waited nearly two weeks before I talked to him.

“You do know I am transgender right?” I asked

COMPLETE SILENCE for nearly fifteen seconds.

“No, I mean…no, oh, really?” followed by another awkward pause.

I could tell he was uncomfortable and needed to pull back.

“Look, its fine, I have to go anyway, I had fun though.” I said and then hung up the phone.

Wow, what do I have to do to have a relationship? Tell them, don’t tell them, it doesn’t matter. And just like that I found myself sliding into my first bout with depression since beginning to transition. And no, he did not call me back that day, or the next day, even the next week but eventually… I get a text.

“Kendra, I am sorry I didn’t call you back but honestly, I am having a hard time dealing with this.”

“Don’t worry about it Jerry, I am not stressed about it, you shouldn’t be either. I wish you the best though.” I replied.

“No, I see you as a beautiful woman; I want to take this slow but, I do want to see you again.”

This time it was my turn for the awkward silence. I waited until the following day to reply.

“Meet me for lunch on 14th street, after my therapy appointment.”

And just like that we had our second date, and third, followed by that uncomfortable conversation about sex. “I am good with oral sex, you know giving, and that’s it, well for now anyway. I would really have to like you before I let you fuck me.”

Yea, not a good use of my language skills.

“And if you ever wanted to come to my house you will have to meet Kim and Tony. We kind of agreed to those terms when we opened up our marriage.” They met soon after and everyone seemed to hit it off quite well. In fact the very night they met Jerry, I invited him to spend the night.

I used to tell Kim and the guys on dating sites, even guys I went out with, “I missed out on being a teenage girl, I really want that experience, I actually kind of need it.”

Okay, so I wasn’t exactly getting that with Jerry but it was as close to it as I could get without it feeling fake.

At this point you might be asking, “Where the hell am I going with this? This sounds like a journal entry and not an actual review.”

Ha, it’s both, gotcha!

Let me give you a little taste of what it is like to be Kendra on any given weekend, for example last weekend. Twelve A.M meet up with Jerry, watch a movie and followed closely with “enjoying each other’s company.”

Asleep by 5AM

Wake up at 9 for Maryland Renaissance festival, spend the day with friends and family watching shows and eating and then a transgender dinner and get together in Virginia only to rush home and be at work by midnight.

Asleep by 9AM

Up by 1PM to watch the Dolphin’s game with Brendan. Get dressed and rush off to Virginia to have dinner with my favorite couple-Marcie and Jamie followed by stumbling home because of living off of 7 hours of sleep over the previous two days.

Think it is over? Not by a long shot…

Monday work gets paired up with my committee meeting for the EAC…and yea, work was busy. Go, go Tuesday, rush to D.C for my early transgender appointment, fight for parking and speed home for work.

Want more? My life is like that 90 percent of the time.

See Kendra Chelsea is God’s own personal reality show. “Hey Jesus, get in here! You will never guess what I threw in Kendra’s lap this time.” God booms.

“Jesus…H….Christ dad…” Jesus answers

“Hey, don’t you use your name in vein…not cool…”

Hey Kendra….It’s me, Kendra, from about 4 in the future….”Remember when you wanted to help people? Remember when you thought no one would ever love you? That being transgender was going to be your downfall?"

Well don’t be stupid Kendra; okay, so your mom doesn’t want to see you and okay, so you are going a little gaga over a handsome, well-cut man who seems to be saying all the right things…Kendra, you are one lucky bitch, do your friends and family a favor and shut-the-f-up and enjoy the ride.

The Future

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