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Songbyrd: Becoming She

The Editor | Feb 6, 2017

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By Caisie Breen

“I want to be her.”

I pointed to the skinny girl on the cover of an AdvoCare diet magazine. I couldn’t believe I said it — not only once, but twice. I was in Portland, Oregon, at the home of my sales rep Penny, picking up a new order of products. Pushing fifty and becoming very self-conscious about my weight, I was selling diet products to save money on my orders.

Penny was taken aback. “Don’t we all want to be that skinny?”

“No, I want to be her!”

Penny had a troubled look on her face as we exchanged goodbyes. When I got in my car, I was embarrassed and almost went back to apologize. What was I thinking? My comment surprised me as much as it surprised her. I decided to forget about it and hoped she would, too.

This was a horrible thing to happen to a conservative Republican like me. I opposed gay rights and had campaigned against them in an Oregon referendum, strongly supporting religious “traditional values.” And yet, a feminine side was seeping into my life — some of it consciously, some not. I decided I wasn’t going to tell my wife, whom I affectionately called “Brenda Sweet,” what I’d said.

Our two boys, Ryan and Brandon, were still in grade school. Our home was a light yellow, two-story, remodeled Cape Cod in the suburbs with a large yard and a white picket fence.

When I got home, our dog Rachel ran to my car, barking. She was a golden retriever mix, just large enough to knock someone down if she was excited. She was excited.

“Oh Rachel, Rachel. No — down, down!” I laughed as she tried to lick me into forgetting that she’d escaped from the house. I took her inside and had a talk with my son about keeping her indoors.

“Hi, honey. What’s up?” I asked as I plopped myself into our sofa chair.

“Weekenders,” Brenda answered. “Don’t you remember? I have seven women coming, and they’ll be here in an hour. I’m afraid you’re going to have to make yourself scarce and leave for a couple of hours, or stay in the back. If you stay here, you’ll have to be invisible—they’ll be changing in the living room and bathrooms.”

Weekenders was a home-based party plan for selling casual women’s clothes. “Oh that’s right,” I said. “I forgot. I’m going to hang out in the back.”

Brenda’s women’s clothing shows enticed me. I occasionally used women’s clothes during sex as an enhancement. Before our boys were born, we would explore gender role-playing at our favorite weekend beach getaway in Lincoln City. We always made a stop at the local thrift store to check out soft and silky undergarments to liven things up. One weekend had really gotten crazy.

“Hey hun,” I’d said. “Check out the black stockings over in the markdowns. There’ are even some matching garter belts in there. Will you get them for me, please?” I was too timid to grab them myself.

“Sure,” Brenda said with a giggle.

I stood in the men’s aisle next to the bin of stockings, watching Brenda’s every move and becoming overheated. Fantasizing about what our evening would look like lowered my inhibitions.

I left the men’s aisle and slowly walked up behind Brenda. She was still slightly bent over, rummaging around in the large bin full of stockings and wigs. I placed my hands on her shoulders and gently moved my pelvis up against her butt. I did my best to keep my movements discreet, but I was euphoric and didn’t care if someone saw me pawing my wife.

I pressed my pelvis a little harder.

“Oh my God. You’re driving me crazy,” Brenda said.

“That’s the plan, my Brenda Sweet. I’m all yours tonight!” I whispered, slowly grinding.

“Oo, oo, oo! Yes, you are. You’re mine tonight! And you’re going to do anything I say, right?”

“Absolutely, sweetie. No questions asked. Absolutely,” I said like a well-trained puppy dog.

By the time we left the store, I was feeling softer and more feminine than I had in years. The motel was only minutes away, and when we walked through the front door, I said, “Okay, babe, will you do me up with makeup tonight? I want to be pretty.”

“Really? Okay, sit right here.” She pointed to a small table next to the bathroom. “Now, I’m going to put a little eyeliner on you.”

She applied a thin stroke of eyeliner at the base of my eyelashes, and then continued applying makeup to the rest of my face. With each stroke of a brush, I felt a delightful zing.

“There. Oh my. Go look in the mirror, honey,” said Brenda.

I looked in the mirror and saw that she was right — I was gorgeous! In my head I was singing Walk on the Wild Side: “Plucked her eyebrows on the way/Shaved her legs and then he was a she/She said, hey, babe, take a walk on the wild side/ Said, hey, honey, take a walk on the wild side.”

“So what do you think?” Brenda asked.

“Come here, my Brenda Sweet,” I said. “I’ll show you what I think.”

We spent the next hour having sex, playing lesbian lovers. Brenda and I were both beautiful and so in love. We embraced and kissed until I exploded in total bliss, which immediately dissolved into feelings of guilt and shame.

“I need to get this shit off my face, now,” I said as I ran to the bathroom. From the time I was at the thrift store to the time I climaxed, I had felt feminine and beautiful, but now I just felt ashamed. This struggle wasn’t new, and it wasn’t the last time it would happen.

And now I found myself wanting to be part of Brenda’s Weekenders party. But what an insane thought — to be a part of it? What was I thinking? This wasn’t a sex game, playing femme. This was a women’s clothing party.

“Okay, Bill. I need your help,” Brenda said. “Will you get the card table and set it here against the dining table? And we need snacks. Can you fix us a veggie tray, sweetie?”

“Sure. I’ll get right on it,” I replied.

Just as I put the veggies out, the first party guest arrived.

“Oh you. Shoo, shoo,” Brenda said to me. “Time to make yourself scarce — and thank you, honey, for all your help.” She gave me a big kiss.

I went to my hideout at the rear of the house, kicked back, and began reading my paperback, Anne of Green Gables. As Brenda’s party guests arrived, I couldn’t help listening in on the conversation and fun.

“Oh look, Brenda!” said one of the party guests. “This is exactly what I wanted at your last party, but you were out. And they even have it in green!”

“I know, Diane. And check this out. The Little Red Dress!” Brenda said.

“I want, I want! My goodness, Brenda, that’ll look gorgeous on you. It’s the exact same cut as last year’s Little Black Dress. I’ve got to have one,” Diane said.

I felt a strong urge to go out and see some of the clothes everyone was so excited about. After all, my male wardrobe consisted of just four pairs of jeans, all blue, and five or six short-sleeved shirts.

Just before I peeped out the door, Brenda came rushing in with an armload of clothes to try on.

“Hi, honey. Both bathrooms are occupied, and I need to try on this Little Red Dress.” She pulled her top off, slid out of her pants, and had that pretty little dress on in less than sixty seconds. She held her arms out to the side and asked, “How do I look, honey?”

“Wow! Dangerous as hell. Seriously, it looks gorgeous on you,” I said, laying my book down.

“Aww, thanks, sweetie.” Brenda kissed my cheek, put her clothes back on, and rushed back to the party, leaving the Little Red Dress behind. I grabbed it, held it up against my chest, and looked at myself in the full-length mirror. I felt a lump in my throat as I saw how beautiful I was.

I slowly laid the dress down across a chair. Bill Casey, beautiful? How could I look so wonderful and yet feel so dirty? I felt a sense of loss as I listened to the girls giggle and talk about the clothes. It seemed that there was such camaraderie with women, whereas in my male world, I always felt I was in competition. When I was younger, it was either who played the best sports or chugged beer the fastest, and as adults, it was who made the highest sales among our employees. These women were talking about each other’s families, current dress styles, makeup, and color combinations. I longed to be included, but that wasn’t to be—not at that party, anyway.

After the last woman left, my Brenda Sweet came back to get me. “Hi, honey. You can come out now. Everyone’s gone.”

“How’d you do?” I asked.

“Pretty good. Everyone bought at least one catalogue item. And how about you? Did you get lonely back here by yourself?”

“‘You know, honey,” I said. “I know this sounds weird, but I found myself wanting to be part of your party. I heard you all having such a good time.”

Brenda smiled her sweet smile. “I understand. Of course, you would want to be a part of it—we had a blast. But there were women changing clothes; you know it wouldn’t work.”

I wanted her to understand. “That’s the crazy thing, dear. I began imagining myself trying on those clothes with everyone else. And there wasn’t anything sexual about it at all. I could see myself going through the different colors and styles, trying on what I liked, like everyone else, and it felt great; it felt natural. I know. Weird, huh?”

“Wow. That’s a leap, all right.” Brenda thought for a moment. “Tell you what. Why don’t we do a little dress-up party occasionally here at home for you, and see what happens? If this is something you want, I’ll see what I can do about future parties.”

What an amazing and confusing thing: a politically conservative anti-gay cross-dresser. But if anyone had told me then that I was transgender, I’d have dismissed the thought. Not me! I just wanted to do girly things once in a while.

Holding that dress up to my body in the mirror caused me to recall a much earlier day of dress-up. I’d kind of forgotten the incident when I was five, with my sister’s cute pink dress.

Chapter 2 will be coming to TGF in a few weeks. If you can’t wait to read it you can buy Ms. Breen’s book now on Amazon.