Innocent Love & Honest Fumbling

Updated: Mar 12, 2019

By Evelyn Sheldon

Illustration by Sophie Lane

I don’t think Eve needs much of an introduction. She speaks for herself. I met her years ago and soon after we became Facebook friends. She writes her experiences and her conscience on her page bravely and without fear. After reading a few particularly eloquent and enlightening posts of hers, I knew I needed her voice in this publication. She is passionate and smart and insanely talented. Without further ado….


My name is Evelyn. I am currently a 45 year-old woman in the early clutches of middle-age, but this is no middle-aged story. This story begins back when I was 20 years old, still a virgin, and attending a small liberal arts college in the Midwest.

This is the story of Cayla, the first woman I ever loved.

My sophomore year, a faculty member’s younger sister transferred to our school from Louisiana. Her name was Cayla. Now, I don’t know what you have or haven’t heard about Southern girls, but this girl didn’t fit into any those boxes. Yes, she could be sweet. Yes, she had a friendly and impish Southern drawl. But she was SHARP! And she was funny! She had a wit, a spark to her…she was SO clever. The way she played with words was a joy to hear. Just hearing her speak would make me feel all buzzy inside.

Luckily we had choir together, so I got to sing and talk with her five days a week. And as we got to know each other, I learned that this natural writer and performer was actually working on a Pre-Med degree: one that she didn’t want, but her father did. She was brilliant enough to pull it off, but I could see her heart wasn’t in it. I was a pretty lost soul those days, and I guess I related to her reconciling the person she wanted to be with the person others wanted her to be. Soon I found myself carving out any time I could to be around her. As the year went on, she became my dear friend, confidant, and playmate. And in our quiet moments especially, I could tell she felt the same way about me, too.

I can pinpoint the exact moment we fell in love: it was summer, and we had just spent a lazy, joyous day with friends in the city. We had gone to a free concert in the park and afterwards it was time to get back to campus. We were lucky enough to have a friend who had a convertible (!), and we got a ride back with him and his date. Cayla and I sat in the back seat, laid our heads back, and rode the whole way looking up at the clear night sky and at the highway signs that would zoom over us so fast that we gasped. Then we started laughing. And we LAUGHED! We laughed so hard and true. We giggled like schoolgirls in that back seat. Halfway home, her hand found mine, and I guess we weren’t laughing at anything anymore, just laughing from the sheer crazy joy of falling in love…in that very moment, on that warm and magical summer night.

Love, for us, was like being in a new and glorious country for the first time and we explored it together. We discovered the love that is long drives, both of us singing along with the radio…her with her legs crossed, feet up on the dash, so comfortable with herself. We discovered the love that is kissing your best friend. And we discovered the love that is sitting quietly in a room together, with no words needed. I would be reading my music history books, she her biology books, and maybe I would sit on the floor while she sat on the couch. I would lay back on her legs and we would smile for the simple joy of being in the same space together. Just being in each others’ presence was enough. Sometimes it felt like we didn’t have a care in the world, except for each other.

That kind of love.

Now, remember, I was still a virgin and so was she. 20 and 21 years old…I know, I know! But this was a different time, a slower time. We began to discover each others’ bodies, touching each other with meaning and wonder. We each had special things about our bodies that moved the other: she would get shy when I would tell her how much I was stunned by her dancing eyes and her mischievous smile and I would blush with pride when she would hold my hands and tell me how lovely, beautiful, and delicate they were. Over that summer, our love bloomed and progressed to the point that we were finally ready. We wanted to explore our love together, to try to use our bodies to make each other happy, to feel good, and to feel loved.

We began to discover each others’ bodies, touching each other with meaning and wonder.

So we talked about it, and talked, and talked some more. And finally, we chose a day. (Yes, we ACTUALLY chose a day…how cute is that?!?) When that day came, we had a sweet and nervous date, and then that night, on the beautiful, secluded lawn under the water tower on the edge of our small town, we laid down our blankets, snuggled in, and tried.

But I couldn’t do it. I couldn’t let go and do what we both wanted so badly. It wasn’t possible for me then, because, to let go, I needed to feel love and kindness towards MY body as well as hers. And that was something I couldn’t do. We held each other and promised it was alright, that this night just wasn’t our time. We were in love, and we would find our time soon.

This innocent love and honest fumbling happened over twenty years ago but it still touches my heart today. And while it’s true I was Cayla’s lover, and that my name is Evelyn now, that wasn’t my name back then. Back then I had a different name. A boy’s name.

I wasn’t Cayla’s girlfriend, I was her boyfriend.

I am, and was, transgender.

Too many years after that first finding of love, I finally found the knowledge, the will, and the hope I needed to transition to living my life as a woman. Today I’m a happier, stronger, more vulnerable and more real person than I have ever been in my life. And I can’t help but wonder: if I had known and understood who and what I was back then, and could have told Cayla…what could our love have been?

The night under the water tower didn’t work out, but I eventually figured out the whole using-the-penis thing, and it was fine. Because I made it fine. But those first few times we tried, it just wasn’t right. And not in that way that it maybe doesn’t feel right to anyone their first time. It didn’t feel right because, well, it wasn’t the part I was supposed to play.

Since I’ve transitioned, one of the saddest things I’ve had to reckon with is the fact that, although being trans has given me rich insights and valuable gifts few people receive (and I’m thankful for that), it also takes from me. By it’s very nature it discolors my past experiences and actions, because I wasn’t (and couldn’t be) FULLY there when they happened. Because a huge part of who I am was so buried, I could only see it’s shadows.

So this is the cautious and emotionally dangerous dance that I have learned to do with my giant lists of “what-ifs”: in looking at my past, it’s essential that I find balance, or the past will crush my present. Yes, I can be sad about not being born with the body I was supposed to have, and I can regret how long it took for me to truly understand that and act upon it, and I can wish that I could have started living as a woman years ago. But I also need to acknowledge that some of the most formative experiences I had before I transitioned: the first love, my music career, my marriage, my daughter...maybe they couldn’t have happened at all if I had transitioned earlier.

When I get upset about what appears to me (in the moment) to be my “wasted past,” it’s helpful for me to think that everything I’ve been through has brought me to this moment. Being trans is complex; it affects everything about me and every part of my life. As a result, my memories are always going to be gently haunted by the “Evelyn” that could never “be” in that time and place. That is my lot in life. But I try to remember that, although I was compromised, it doesn’t make anything that happened back then less real or important. I just wonder what could have been if I had been “myself” all along.

No answers, unfortunately, only questions. But however it came about, Cayla and I had a powerful and adventurous first love, and to this day it is still one of my most cherished memories. The love we had was a rare and beautiful and valuable thing, regardless of my identity. Love is an absolute gift, wherever and whenever we find it. And truthfully…if I had been a cute and happy college co-ed named Evelyn, would we have even fallen in love at all?

I wish I knew.

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