"Roling" Through Life


Matt’s death leaves Skip with a decision to make. Can he be honest one last time?


"Roling" Through Life
By Angela Rasch

I clicked my cell phone shut, tears already burning my eyes.

“Matt had a heart attack,” Amber had said. “He died peacefully in his sleep. We’d like you to say a few words at the funeral.”

I gazed at a post-it note on the refrigerator reminding me to buy yogurt, trying to make sense of it.

I had rested in bed next to him many times watching his chest rise and fall, and had sometimes wondered if I could possibly stand life without him. Amber had been his wife the past thirty-five years, but I had been his best friend that entire time - plus the nineteen years before they got married. He and I had hit it off the minute we met in first grade. .

I had been conflicted all those fifty-four years -- a petite, feminine woman in the body of an all-state fullback.

“Roling” is what Matt had called what we did; gaining perspective by stepping out of our day-to-day lives into much different “roles.” He gave my “roling” (and his acceptance of it) a higher correctness than maybe it deserved.

We had pinky-sworn in the fourth grade to always be “George Washington” honest with each other. Our friendship had survived despite the pain our mutual candor had caused.

“Skip, it’s your breath,” Matt had told me in junior high, when I had trouble connecting with Cathy “Sleeping Turkeys” Urness. She had developed while the rest of us were wondering what went on in the water tank after the girls got naked on “Petticoat Junction.”

I had returned the favor a few years later while taking a shower after football practice; Matt had asked me for an opinion of his endowment. “Your cock is about average-size, maybe a little smaller,” I had responded, with just a touch of amusement behind my frankness.

That frankness would lead to a disclosure of my cross-dressing, which had, until that time, followed a typical pattern; a furtive, lonely venture marbled with guilt and self-humiliation. June wasn’t the kind of person who would accept or understand the side of me I called “Cynthia.” To keep our marriage sound, and for the sake of the children, I never indulged myself within our home. June had died in a car accident eight years ago knowing nothing about the real person inside me.

Only one person knew about Cynthia, and he had just died.


“God it’s great to get away for a couple of weeks,” Matt said, his nostrils flared as he sucked in the pine-scented air of the north woods. “The walls were starting to push in on me.” It was the first vacation for just the two of us. Both of our wives had said they were too busy with kids’ soccer, baseball, and other things to get away.

He had just told me that Amber and he were in counseling, trying to save their ten-year marriage. Pictures of his twin boys, Teddy and Noah, rested on the top of the beer cooler between us. They would enter the third grade that fall.

He frowned. “The sex isn’t so good anymore, what there is of it.” He stared out onto the lake, which was taking on a golden tone in the late evening sun. We had rented a secluded one-bedroom cabin. It was so small it only had one bed. This didn’t bother us as it was big enough so we didn’t disturb each other’s sleep.

The location’s main attraction was total privacy. The forest created a world for just the two of us, with only those outside influences that we wanted to bring in to break the peace. “Sometimes I just can’t maintain an erection. Amber thinks I’m not sexually attracted to her anymore.” A stiff night breeze switched directions and blew smoke from the campfire directly toward us.

The total discontent on his face matched what I’d seen in his home. His boys were beginning to have interests of their own and no longer did everything they could to please their dad. He seemed proud of them, but often emphasized their faults in conversations with me.

According to Matt, Amber was severely lacking in a number of key areas. He rarely found anything to compliment and often bickered with her when I was around.

“You and June seem to be so happy. How do you do it?”

I laughed. “I’m just better at hiding my problems than you are.” I had nearly failed a life insurance physical the previous month due to high blood pressure. Hiding my “problem” extracted its price.

Matt snorted. “The biggest problem you have is finding more tax write-offs.”

My business was doing quite well. I sold athletic equipment to schools. I had parlayed my college football fame into a career. My fame got me in the door; and my business acumen kept me there. At times it seemed like everyone in the three-state area wanted to buy their wrestling mats and football helmets through me.

“You’d be surprised,” I said with some frustration. My mind drifted to that pale-blue sundress I’d seen in the window of a dress shop in the last town we’d passed through on the way to the lake. No doubt I would find something like it on my next business trip. I would buy it and enough other articles of feminine clothing and makeup to satisfy my urges. After transforming myself in a hotel room, I would spend a quiet evening wishing I had someplace to go and someone to be with who would appreciate me.

“I would only be surprised if there was something I didn’t know about you. We’ve always been open and honest with one another.” He smiled that huge, goofy, lovable smile that covered his face when he spoke of the bond between us.

I grabbed another beer from the ice-cold water in the cooler and hid my guilt by peering into the dying embers of the fire we’d used to pan-fry our walleye and pike. Sure, he knew all about “Skip,” but he knew nothing of Cynthia.

“I do know everything about you, Skip, don’t I?”

He could always read my mind. I had almost told him about Cynthia a hundred times. One time during our senior year in high school, when my parents had gone on a business trip and left me home alone, I had bought a dress and some other things. I had intended to ask him over and meet him at the door as Cynthia. I had chickened out when I tried on the dress and found it didn’t fit. It was a size fourteen, the biggest they’d had in that store. I later discovered I wore a 22W.

I opened my mouth to lie to him once more, but couldn’t make a sound. Perhaps I’d reached the maximum level of deceit our relationship would stand.

He turned toward me. “There’s something you’re hiding from me . . . I can tell.” His words had been spoken so softly they barely reached my ears, yet they shattered my heart. It was clear that our friendship, or at least that kind of special friendship we enjoyed, was at stake.

“Matt, there is something you don’t know about me.”

He remained quiet. His silence shamed me further as it indicated his complete faith that eventually I would tell him.

I took a long pull on my beer before I continued. “It’s time I told you, but I can’t do it tonight. Tomorrow I want you to go out on the lake by yourself and fish for about eight hours. When you get back, don’t come into the cabin until you’ve cleaned the fish. When you go into the cabin to put the fish in the refrigerator, don’t dawdle. Go in, leave the fish, and then go down to the lake for a swim to clean up. Have a couple of beers while I cook dinner. I don’t want to see you until we have dinner; then I’ll tell you my secret.”

“What?” His one word asked me dozens of question for which there were no answers, so I elected to ignore it.

I looked him in the eye. “Out on the lake by ten, stay there until six, clean the fish, and stay out of the cabin except for putting the fish in the refrigerator. Got it?”

He nodded. I picked up the cooler and headed for the cabin with my mind spinning. I had sent myself down a dangerous path, but one our relationship demanded that I take.

The next morning I left for the nearest town. I arrived as the stores were opening. I had long ago lost the fear of openly buying what I needed. The town was large enough to have a plus-size women’s clothing store, a drug store with a good cosmetics department, and a store that sold good quality wigs. I had decided not to hold back. I would go the whole nine-yards and dress from the skin out.

I selected a dress made of a soft fabric -- fashionable but not too formal. I could have worn it to a P.T.A. meeting at the boys’ school “if” . . . That “if” had driven me crazy all my life. I picked it because I knew its bright yellow would look good with my dark skin and my auburn wig.

I always bought a wig first. It was the hardest purchase to make as there was no way to say, “It’s a gift for my wife.” Evidently wig salespeople have seen it all because no one had ever questioned me.

I found a pair of two-inch heels that went with the dress, and then spent about an hour picking out make-up and the right scent. I didn’t want to wear any perfume that June or Amber had ever worn. I settled on Pavlova. The woman in the store said it had been very popular in the twenties, but had only recently been revived.

My purchases included fake fingernails and polish, powder and bath salts, lingerie, stockings, and enough jewelry to complete the picture. I loved clip-on dangly earrings and bracelets.

As I drove back toward the cabin, I made an effort to calm my mind by forcing myself to adopt a completely feminine spirit. Matt was still my best friend. I loved him as I always had. Nothing had changed, except I wasn’t going to hide behind a false exterior. By the time I reached our vacation spot I had shoved Skip into the background and was fully into Cynthia mode. I couldn’t wait to take a long perfumed bath and prepare for the evening with Matt.

As I was putting the finishing touches on my perfectly applied make-up I heard the front screen door slam.

“Honey, I’m home,” Matt called with good humor. “I’ll just put the fish in the fridge and go on down to the lake for a swim. Call me when dinners ready.” The screen door slammed once again.

I went to the kitchen feeling gorgeous, and then cooked what I knew would be a delicious meal of baked fish and steamed vegetables. When everything was done, I flicked the switch next to the front door twice. That switch lit a small light on the dock. It was our signal to one another that dinner was ready.

I was putting the last dish on the table when Matt walked in.

“Hmmm,” he said. Looking me over from head-to-toe.

I blushed. My legs had turned to lead. I had to sit, and did so as elegantly as I could. I felt every one of my two hundred pounds and seventy-four inches. How could I be so asinine?

Matt picked up a fork and started in on his walleye. “When I brought in the fish I caught a whiff of your perfume. I figured your secret was something like this. Pass the butter please.” He calmly buttered his bread as our friendship eased forward into a new era.

Every year after that, Matt and I brought Cynthia along on our summer retreat. We would go back to that same cabin for a week by ourselves. I would bring enough clothes to spend the entire vacation, day and night, as a woman. Matt treated me as sweetly as I could have ever hoped. Every once in a while he would go into town and buy me flowers, for no particular reason, other than “a pretty woman should have flowers around her.”

I did all the cooking and cleaning. Matt caught most of the fish, although he did take me along whenever I wanted to go.

My hobbies during that week were sewing, knitting, and crocheting; and I brought along romance novels and women’s magazines to read. Matt made trips to the small liquor store a few miles down the road for white wine as well as for beer for him. I never went into the town. I didn’t need to — I would plan our week meticulously each year so that nothing was left to chance. A trip to town would only break the spell we cast on each other regarding my appearance.

I watched my weight for months prior to our vacation so that I could fit into fun things. The knowledge that we would have our week together alleviated the heartache I endured the rest of the year because I couldn't dress when and where I wanted. My blood pressure went down and my outlook on life improved drastically.

And now — he was dead.

I decided to drive the 200 miles to the funeral and spent the time on the road thinking about Matt and honesty. My thoughts directed me to an inevitable conclusion. There was no way I could go to his funeral and not be totally honest as my true self, one last time for Matt.

After I reached the city where Matt had lived, I made a shopping trip like I had many years ago at the lake. In a sentimental gesture I bought Pavlova, its aroma still as soft, delicate, and romantic as I remembered. My dress this time would be the traditional mourner’s black wool.

As I walked into the church, my heels clattering on the tile floor, I heard muttering all around me. I didn’t lock eyes with anyone; what I had to do was between Matt and me.

I took a seat toward the front so that I could get up quickly for my eulogy. I had barely settled in when Amber slid in next to me.

“Skip, what the hell are you doing?” Her voice came out of her mouth like steam escaping a teakettle.

A young man, who had to be a tenth generation funeral director, pushed his hand out to me. “I’m William Wilson.”

I smiled at him. “Cynthia.”

“Cynthia?” Amber grunted. “Good God, Skip. Are you crazy?”

The pasty-faced young man patted Amber’s hand. “We all grieve in different ways.”

Amber yanked her hand away. “You don’t mean to say you think I should let her . . . HIM stay?”

The unctuous undertaker turned toward me again. “Cynthia, are you sure you want to be here.”

I nodded in answer to his question. “Matt was my best friend, and I need to do the eulogy.”

Amber glared at me. “If you want to turn your best friend’s funeral into a travesty and make a complete ass out of yourself at the same time, no one’s going to stop you. Wilson, get this thing going before someone comes in with trained jackasses.”

When called, as Skip, I made my way to the pulpit to speak about Matt. The mumblings around me swelled and threatened to drown me out, until the minister stood and asked for silence.

I calmed myself and started again. “Matt was my best friend for almost my entire life -- starting in grade school, and on through college where we roomed together all four years. Up until today, Matt was the only person in the world who knew that I’m transgendered.

“A month ago Matt wrote a letter to me that I would like to share with you.”

I took two, folded pieces of paper from my purse. Outside, a meadowlark sang its sweet chorus. I dared not look at what I knew were openly hostile faces. My thoughts zeroed in on doing what Matt would expect me to do. There would be plenty of time to collapse in tears later on.

“Dear Cynthia,

"In a few weeks you and I will spend another week at the lake. You, no doubt, will look lovely once again in a new dress or two. You never fail to amaze me with the total transformation you make, from the Skip I’ve always known, to the Cynthia I’ve loved for all these years.”

Several people gasped, but I found a way to continue, even though my tears -- tears prompted by my reaction to his unique handwriting — blurred the words. The sincere honesty I had shared with Matt wasn’t going to bend to those in the church who couldn’t stand the sight of me.

“You’ve often told me how much our trips together have meant to you. You’ve thanked me profusely for allowing you to grow as you’ve spread your feminine wings.

“It’s way past time for me to say ‘thank you’ to you.

“That first time when I met Cynthia at the lake I was at a crossroads. I didn’t think I loved Amber anymore, and I had almost no interest in my kids.

“As we had often discussed, I was demanding absolute perfection from them and would accept nothing less.

“Amber is the best thing that ever happened to me, and yet I was ready to divorce her. If Amber wasn’t good enough, I would have never found happiness and would have become one of those tragic men who never find love because they’re too blind to know they’ve already got it.

“That first night I had to fight my anger toward you. I wanted to punch you in the face for testing my beliefs about gender. I wanted to straighten you out by saying horrible things. It wasn’t easy to see my closest buddy from an entirely different perspective. Those years and years of placing such a high priority on honesty between us prevented me from going off on you. How could I be mad when you were being more straightforward than either of us had ever imagined we would have to be?

“In one intense and defining evening you taught me both tolerance and compassion. I suddenly realized that people could be different than what you expect and still be wonderful.

“It was an epiphany that I took home and used to turn around my life. I quit trying to force the boys to do things for my personal gratification. Once they were allowed to find their own direction, they flourished. Amber’s quirkiness became lovable once again — as it always should have been.

“That isn’t to say that I wasn’t scared shitless that first night, especially when you told me you loved me. I can’t tell you how relieved I was when you clarified that statement by saying you loved me like a sister loves her brother, and that there was no sexual attraction. Once you defined our relationship like that, everything fell into place and I never again experienced a concerned moment, although I’ll have to admit I don’t mind the occasional hug and peck on the cheek.

“Cynthia, I owe you so much. I love you.


I folded the papers, and before I knew it found myself sitting in the pew once again. Tears ran down my face, and I was glad I had taken the preventative measure of wearing waterproof mascara.

There was no internment as Matt had requested cremation. The church emptied into the adjoining fellowship hall for a reception. I remained in my pew, planning to slip out without creating any more dissonance. My head down, I silently reflected on Matt and my past. It had been wonderful; something few people ever experience.

I shivered when a small hand touched my shoulder.

“Matt wasn’t the only one preparing for a divorce,” Amber whispered as she settled in right next to me. “I had been to an attorney and had the papers ready. He wasn’t abusive, but I didn’t want to raise the boys in a house without love. When he came back from your trip that first year he definitely was a changed man. From the moment he walked in the door, he looked only for the good in me. Up until then I could do nothing right, after that I seemed incapable of doing anything that didn’t utterly delight him.”

I nodded. I had always known the best side of Matt. Amber was lucky he finally found a way to be as fantastic with her as he always was with me.

I smiled at her; and she continued. “All of a sudden he had become a loving father. When he needed to correct our boys’ behavior, he did so in a positive way. Whatever you did in that cabin made him a different person. I always wondered, but never really had a clue.”

“I did love him so,” I said, choking back the tears.

“And he loved you,” Amber said, taking my hand. “He told me so a thousand times.”

She pulled me from the pew. “Come, Cynthia, so many people want to meet you. Some of the stinkers have left, but that makes it easier to know who’s honest and who isn’t.” She took my arm in hers and held me close. “I heard you sold your business and retired. Have you given any thought to moving here so we can be close?”

In her eyes I saw the reflection of a large woman, the woman Matt had loved like a sister.

Amber’s chatter went on as we walked together toward a new life.

(This story was inspired by a conversation with Dimelza about a new story she is putting together. As I wrote this, I realized this is how I wish “Brokeback Mountain” had been written. Thanks to Kelly Ann and Heather Rose for their help.)


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