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Crushing on Keith (Part 2 of 2)

  • Kendra Chelsea
  • Oct 20, 2016
  • 6 min read

I remember lying in bed Friday morning, looking back at my life after I started transition. I even took a moment to reexamine my life, my fears and hopes over the previous year.

I wasn’t sure if it was me being caught up in the moment or if it was true, Kenneth, his memories were fading away; it was almost as if “he” was a dream that I once had or if reality was just a dream I once forgot.

Like the day I stepped out of my house to go to the grocery store, alone, as Kendra. How I thought I wouldn’t make it to the car without passing out.

Or the day I spent the night in my room, alone, thinking about all the love that surrounded me and coming to the conclusion that no one would ever love me.

Absurdities now but, cold hard facts a year ago.

I remember thinking that life as a transgender woman was both manic and depressive, the lows of thoughts of suicide and highs of being kissed for the first time as a girl. How there were times, as the happiest girl in the world, I thought if one more thing happened during my most depressive moments, I too could end up one of those transgender statistics that make me cry at night.

Yes, even as the happiest girl in the world I can find a valley so deep that I can find myself scared for myself. And then I find the strength to find my place of peace. I think about my best friend, my kids and I somehow, someway find my way back to stability.

And now I am a woman, with a new found respect for females. Females that need to plan outfits, take on intense facial care, put on makeup, shave my legs, laundry and spend much more time on my hair than god intended. And realize I must go beyond that, shave my face, my chest and while actively dating, prepare for sex. (Please for the love of god tell me I do not have to explain that last one to you.)

That was exactly at the point I found myself; checking for stray unwanted hairs, shopping for embarrassing cleansing items and frustrated because the once punctual Ken was now the perpetually late Kendra.

That very first night I spent with Keith was everything I thought it would be and more. To be blunt, I had zero intention of going all the way with him. I would concentrate solely on him and fall to sleep in his arms. But intent means nothing without willpower.

When Keith asked… the only words that would come out of my mouth was, “Where and how.”

In the end, Keith wrapped his arms around me, looked deep into my eyes and kissed me gently on the lips. “Oh, Kendra, Kendra, Kendra, you are amazing.”

I pushed my head into his shoulders and closed my eyes; there was no place in the world I would rather be. I thought as Keith took my hand and almost as quickly drifted off to sleep.

And bless his heart, he snores like a champion. It was nearly sunrise and I had to be up by 9 AM to go to a wine tasting with some friends, Tim and Chris.

So like a good little girl, I pulled myself from the bed, bringing a pillow with me and headed for the couch.

When I finally woke up (what seemed like two minutes later) I stumbled through the living room to the kitchen where I caught a glimpse of Kim, Tony and Keith sitting out of the deck. “This could be either good or bad.” I thought to myself as I pushed open the door and joined them.

“Good morning Kendra.” Tony said as soon as he noticed me

“We were just having a little chat with your date.” Kimberly continued, “He is a pretty smart guy.”

“I think that is why I went out with him.” I answered and then moved behind Keith to message his shoulders. “That among other things.”

And then Keith moved his chair forward and stood up, basically ending the message I was giving him and then went back into the house.

“Keith is coming with us to the wine tasting.” Kim mentioned as soon as Keith was out of sight. “I hope you don’t mind me asking him.”

“No, um, not at all, so I guess you all hit it off?” I asked

“He is…okay…I guess.” Tony replied

“I am surprised how intelligent he is, I guess you can’t tell in a club setting.”

“Good, and oh my god, he is big. I am not used to anything that size.” I kind of bragged and then looked around to see if could be listening. “Okay, where’d my man go.” I said and excused myself to find out.

I found him in my room getting dressed and as soon as he saw me he put his arms around me and gave me a kiss. “I don’t like you telling anyone our personal business.” He said sternly.

“Oh…” I stammered. “You are right, I am sorry, I am kind of used to sharing things with them, I guess I should get used to keeping personal business, personal.”

“It’s okay, it is just that I am kind of a private person, it is just the way I am.”

We all got dressed and piled into one car. I couldn’t help but notice how handsome he was in the morning light. And me being, well, me, I had to document it with a picture. I pulled him a little closer, pulled out my cellphone and started to take a picture.

“I told you Chelsea, I am a private person, I don’t like my picture taken.” He said and then almost pulled away from me but I managed to whisper something just before he got away. “I will make it up to you later if you let me.”

Just like that we had our first compromise, just after our first night together, on our way out on our forth date. Of course it did not stop there; Keith returned home with us after an awesome gathering of friends, spent the night again and took me out to dinner followed by the movies… And we ended our barrage of dates with me falling asleep in his arms Sunday evening.

Okay, what did you expect? …a graphic, detailed, recollection of our sexual encounters? So let me take this moment to be a little honest. I began this journal for those transgender people out there that might want to see what it was like for me to progress through life from the moment I began transitioning to the moment I wake up from surgery…

You know, so they can see it isn’t as bad as their imagination might think. So really, telling you the story of how I learned to take Keith all the way down my throat would neither be appropriate nor be warranted… It isn’t that type of blog so, I wont be mentioning it, not even in passing.

The thing is, even though my emotions were running away from me; even though Keith made me feel normal for the first time in my life, I was fully aware of the fact I was smack in the middle of my second puberty. I knew that how I was feeling wasn’t logical, wasn’t thought out and I needed to be extra careful with getting totally involved with him.

In other words, if I let my estrogen do the talking for me I would have walked outside and screamed. “I AM A TRANSGENDER GIRL LIVING A NORMAL LIFE AND I LOVE KEITH.” But instead I told myself over and over the same thing I told my son Brendan when he started dating someone new. “Kendra Chelsea, you don’t even know this guy, there is NO WAY you love him.

That logical conclusion is most likely the reason I told Keith what I told him when he asked the important question. “Kendra, what are we, a thing or a fling?”

I looked at him and smiled, took his hand in mine and replied. “I think…" I began and then paused to think about it, " I think we are having fun.” And then gave him a kiss on his cheek.

Kendra Chelsea and Keith

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