Chapter 4 – My Dilemma

I could sense that Jamie was excited about something when he called me, breathlessly, late in the evening on Easter Sunday.

“I hope you had a nice day, Perry,” he said, his words coming so fast that they nearly ran over each other. There was something unusually rushed about it.

“Yes, I did have a great day. Thank you, and how was yours?”

“Oh my God, you’re not going to believe this,” he said, his voice rising in both volume and register.

“What?” I asked. “Just slow down and tell me why you’re so out of breath.”

He paused a minute, and I waited patiently, wondering if he’d ever get around to telling me what was on his mind. Slowly, he related that his grandparents had been visiting for the Easter holiday period – a fact he had told me a hundred times, since he loved them so much. He reminded me that they lived just about seventy miles from where I did in our mid-sized industrial city in southern Wisconsin, again a fact he had mentioned over and over, always indicating that if he lived with them, we’d be no more than an hour and a half apart.

“And guess what, Perry?”

“What is it? Tell me Jamie.”

“They’ve invited me to spend the summer with them and we talked it over and my parents are OK with it. Just think, we’ll be together this summer. I can hardly wait.”

“Really?” I said.

“You don’t sound too excited. Why aren’t you excited?” he pressed.

I quickly recovered, realizing he expected his online girlfriend to jump head over heels in joy at the prospect.

“I am excited, Jamie. It’s just that it’s such a shock,” I said, hoping I had sounded more enthusiastic.

Truth be told: I was enthralled with the idea of being a sought-after girl by what I thought was a cute, friendly boy. Trouble was: he still believed I was a real girl, not a sissy boy who was a girl in mind but not body. As he described how we could arrange to meet during the summer, a knot grew in my tummy.

“I already checked,” he said. “There’s a bus to your city that I can take regularly. Or, you can take to come to see me. Gramps said he’d gladly pick you up at the bus station. They’re so eager to meet you, Perry. I’ve told them so much about you and they’ve seen your picture. They think you’re just the cutest girl.”

“Even cuter than Mary Ann?” I chided him.

“She can’t hold a candle to you, Perry,” he said.

“I don’t know about that. She looks awful cute to me,” I said honestly. He had shown me several pictures of the girl, including a selfie of the two of them sitting together at a high school basketball game and they made a truly handsome couple. At my encouragement, the two had been dating fairly steadily, but Jamie kept saying it was only because I urged him to do so. I knew his budding friendship with Mary Ann was helping to draw him out of his shell; he was obviously a much happier boy.

“Well, she’s all right,” he finally acknowledged. “But don’t change the subject. I’ll be up by you this summer and besides I like you the best.”

“OK, Jamie. Have it your way, but don’t get too interested in me. You might not like me when we meet in person and I can tell Mary Ann is a sweet girl for you.”

“Don’t say that, Perry. Don’t you like me?”

“Let’s not go there now. We’ll talk more about this later, besides it’s late now.”

He grudgingly agreed to say goodnight. Our usual closing kiss was much shorter than before.

*****

When I told Cindy about the phone call the next day, she had begun to raise my suspicions about Jamie, planting a fear over the boy’s motives and also if he was really who he said he was.

“Something seems wrong about that guy, Perry,” she said. “Wasn’t he talking about marrying you almost right away?”

I had admitted that he had done that, but I just thought it was idle boy bluster at the time and dismissed it.

“Well, what kind of a boy would propose to someone he never even met?” she reasoned.

“I didn’t take it seriously, Cindy,” I said defensively.

“I’d be wary of him, though, and I wouldn’t be so eager to meet him,” she continued. “Who knows what he’s after? Maybe he’s an axe killer or he’ll molest you.”

“No, no, he’s not like that at all, Cindy,” I protested.

“Well, just be careful,” she warned.

“Actually, Cindy, there’s something else that bothers me even more. He still thinks I’m a real girl, and I don’t know what he’ll do if he ever finds out about the boy thing.”

“You’ll have to tell him, Perry,” Cindy said, “and do it before he ever meets you in person.”

“He wanted me to be his girlfriend. Oh, he’s so sweet and sincere, how can I tell him and disappoint him?” I asked, pleading with her to somehow come up with a magic solution. “There’s gotta be a way, Cindy.”

“No, honey, there isn’t,” she said firmly.

"And you know, Cindy, I felt I loved him, like I was a real girl in love with a wonderful boy.”

“You really felt deeply about Jamie, I could tell. Yes, dear, you’re a girl in love.”

“But that’s just it. I am not a girl.”

I began to cry; we were sitting together on my bed and I collapsed into her arms and she hugged tightly, rocking me as a mother would do to calm a crying young child. Finally, I broke from her warm, loving grasp. Cindy helped me compose myself, using several tissues to dry my face; she fixed my makeup and I felt a little better.

“I know what I must do, Cindy,” I said, my voice taking on a firmness that surprised me. “I’ll tell him tonight. Everything.”

The next eight hours before our scheduled call dragged by slowly, every minute seeming to weaken my resolve. Maybe I should just fade into the woodwork and slink away never to be seen again, leaving Jamie to wonder what became of his online girlfriend. No, that wouldn’t be fair to a sweet boy who presumably loved me. No, he didn’t love me, Perry, the sissy boy; he loved Perry, the fake girl.

*****
It was with trembling fingers that I sent a text message to Jamie early in the evening. “Jamie, let’s talk on Skype to night. OK?”

Almost immediately he replied: “Sure. Going to wear something sexy tonight?”

“I got to show you something.” Was my only response.

In preparation for the call, I decided to wear only a pair of sweat pants and a red Wisconsin Badger sweatshirt. I put on no makeup, and tied my hair in a ponytail, hoping to make myself as ordinary as I could, perhaps even to look more like a boy. In addition, I located my high school yearbook from the previous year that depicted the boys’ cross country team, with me standing in the back, clearly identified as Perry Periwinkle, sophomore. I dropped out of cross country in my junior year, largely due to my failure in keeping up with the others, but also because of my growing girlishness.

Jamie was shocked at my looks when we both signed on. He wasn’t mad, but the dear sweet boy was worried that I was sick. His concern for me was so touching, I almost gave up on my resolve to tell him the truth.

“No, Jamie, I’m feeling fine, it’s just that I need to tell you something. And, it’s important.”

I could see him scowl, apparently wondering what I was going to say. He had never before seen me so roughly dressed. I had always dressed for our Skype sessions in a lovely top of some sort. Recently I had taken to wearing not much more than a cami so as to expose my shoulders and arms. He loved how soft and smooth they appeared.

“Oh? You have a new boyfriend?”

“No, Jamie. Nothing like that. You’ve been my one and only boyfriend. Ever. The truth.”

“What then?”

I decided to plunge right ahead.

“I’m a boy,” I proclaimed firmly.

He looked at me hard for an instant. At first, my simple, direct declaration didn’t seem to register.

“You’re what?” he asked.

“Jamie. Listen to me. I never wanted to deceive you, but I am a boy. I have a penis and everything.”

“No, you’re not. You couldn’t be. My God, your body, your arms and shoulders, so lovely. No boy could be so pretty.”

I started to cry. This was torture for him I could see; it was also torture for me. I loved him so much.

“Don’t cry, dear Perry,” he said. “How could you be a boy?”

“Well I am, even if I’d rather be a girl,” I said. “Look at this.”

I held up the yearbook, open to the picture of the cross country team and set it up so that it filled the Skype screen. “See the boy standing at the right. That’s me last year.”

Looking at the split screen, I could see him squint, carefully examining the picture.

“Oh my God. That is you, but you even look like a girl in that picture.”

“Well, I’m not. Do you wanna see my penis? Do you need proof?”

Jamie shook his head.

“How could you do this? Lie like this? Lead me on?” he asked, his voice suddenly becoming angry.

“I couldn’t help it Jamie. It just happened . . .”

“I loved you, Perry, with all my heart. You helped me so much. Oh this is so bad. What’ll I do now?”

“I’m sorry, Jamie. So sorry. I’ve come to love you and I truly wanted to be your girlfriend.”

“How could you when you’re not a girl?”

“It’s not that simple, Jamie. Let me explain.”

With that his screen picture went black. Jamie was gone.

*****
Mom awoke me the next morning for school. I was still dressed in the sweats and had fallen asleep after what seemed like hours of sobbing on top of the duvet. My face was swollen and puffy, eyes red and watery. My hair was a ratted and tangled mess.

“What happened, dear?” she said, sitting down on the bed.

“Oh mother,” I said, sitting up and wrapping my arms about her in a big hug.

After a few minutes of warm hugs, I told mother the whole story.

Her first reaction was one of relief, even though she knew I was hurting from his rejection.

“Look, honey,” she began. “There was something weird about the boy, the way he latched onto you, even without ever meeting you. I was worried if he’d ever come to see you, not sure what he’d have in mind. Maybe, it’s just as good it’s over. It’s too soon for you to worry about boys.”

“Mom, you’re wrong,” I replied. “He was just a shy, but very nice.”

“Well, you’re such a sweet and welcoming girl, maybe too nice,” she said, hugging me even more tightly. “You have to be more cautious, honey, about opening up to everyone. You never know who you’ll meet on the internet.”

Mom was probably right, but that wasn’t what bothered me.

“Oh, Mother, I was so wrong. I was living a lie, trying to be a girl and lying to such a sweet boy like Jamie. He didn’t deserve me.”

“No darling, when you’re pretending to be a boy, you’re living a lie,” mother said.

“But . . . but . . .”

“No buts, darling Perry. You’re a girl deep inside. I know it and you know it. We’re going to have to do something to see if we’re both right, honey.”

“What?”

“It’s time we see a doctor.”

*****
A week later, my father returned home, this time from Uganda. Mother told me that he had to be told that I was considering living as a girl.

“He’ll be angry as hell, Perry,” she warned me.

“Do you have to, mom?”

“I’m afraid so and the sooner the better. If we wait too long and he learns about by accident he’ll be furious for sneaking around behind his back,” she explained.

I couldn’t argue with that and we prepared for the worst. Mom offered to tell him herself, without me being around, so as to blunt any potentially violent response. I felt I should be present, too, and I should be the one to tell him. For some reason, I felt my dad would be a perfectly reasonable man, even though he worked in a totally macho world among contractors and rough-speaking construction workers. Dad also was a scratch golfer (that meant he shot near par always) and loved being one of the boys. He had tried to get me interested in chasing the little white ball, but I had proven to be just as woefully deficient in golf as I had been with every other attempt I made at sports. I know he was disappointed in me, even though he tried to avoid showing his feelings.

I knew that my dad loved me, and I also knew him to be a person who thought things through and did research before making decisions. I hoped he’d consider the news that I considered myself a girl would prompt a loving and studious response.

We confronted him the day after his return from Uganda, when he’d finally recovered from the fatigue of the long trip back. Returning from school that afternoon, I found mom and dad sitting in the living room. It was obvious they were waiting for me.

“Your mother tells me that you have something important to tell me, Perry,” dad said, after I sat down in an upright side chair opposite the sofa.

My parents looked intensely at me, their coffee cooling on the cocktail table in front of the sofa upon which they were perched. I hesitated to corral my thoughts; the words should have come out easily since I had practiced them a hundred times. Mom had finally agreed with me that I should tell my dad; he should hear it from my lips. I knew my father appreciated straight-forward language.

“Yes, go ahead. I promised your mother I’d try to be understanding, even if I didn’t like what you’re telling me,” dad said, offering a smile that may have been just a bit forced.

“Dad,” I said, “I want to live as a girl.”

He looked back at me, saying nothing. His face seemed to be a blank.

“Dad, didn’t you hear me? I said I want to live as a girl and then as a woman. I am a girl not a boy.”

He still didn’t say anything, but examined me closely and then looked over to mom who sat rigidly, both hands folded in her lap.

“Did you know about this?” he asked my mother.

Mom told him everything, from the moment she caught me in Kelly’s nightgown, including the purchase of some of my own things and our girly nights together while he was traveling. She told him about transgendered women whose transitions occurred because of forces of nature over which they had no control.

“We’ve made an appointment with a specialist to assure that if Perry embarks on this road that it’ll be the right road for him,” she concluded.

“Well, I don’t like being kept in the dark about this, Maryann,” dad said finally.

“Jack, I really wanted to see how real Perry’s desires were. He’s been a far happier boy, or should I say, girl?”

“I’m not ready to accept this, but maybe I have only myself to blame since I’ve been gone so much. A boy should have a man around,” dad said.

“Jack, please don’t reject Perry and turn away from him,” mom pleaded.

“I’m not rejecting him. I’m just going out for a while,” he said, arising from the sofa. I looked at my dad, puzzled as to why he didn’t fly off in a rage, or at least begin telling me how disappointed and disgusted he was at hearing the news. He seemed stunned, a reaction that bothered me more than if he had cursed me out.

“Don’t go, Jack. Please understand,” mom said.

“Think I’ll go to the driving range and hit a bucket of balls, maybe two buckets,” he said. As he reached the door, he stopped, turned to look at me. “You coming, Perry?” he said.

“To hit golf balls?” I asked.

“Yes. Go change your clothes and get those golf clubs you got for your birthday. We’ll go in about ten minutes.”

“You want me to join you?”

“Yes, now hurry.”

I was puzzled and looked to mom. She nodded to show her agreement. After he left the room, mom came over to me and took my hands in hers. She said, “Your father loves you and he’s not a mean man, honey. He needs some time. Be nice to him, dear.”

I nodded, realizing she was right. Dad had never spanked me, had been patient at my ineptitude he took me out to play catch or shoot baskets or hit a golf ball. As I left to get the golf clubs and join my dad, I still felt anxious as to what my father had in store for me.

It wasn’t that I hated golf, it was that I was so pathetic at the game. It was humiliating to be on the course and watch my weak drives compare badly with the powerful pokes of other players. Of course, I was no better that afternoon, but dad worked with me to perfect my swings; he was always patient with me.

Several tee places away from us at the South Range Golf Range, a girl who appeared to be about my same age was smacking straight and pure drives out to the 200-yard marker. She was under the watchful eye of an older man who was likely her father and appeared to be urging her to even longer drives. In the meantime, I was dribbling the ball off the tees and occasionally hitting it solidly, but even those hits barely reached the 150-yard marker. My father watched me closely, and I wondered what he was thinking as he saw my pathetic hits. I wanted so badly to impress him and tried following his previous instructions in how to hold the club, swing and concentrate (“Whatever you do Perry, concentrate,” dad told me. “Concentration. That’s an athlete’s best tool.”)

His own concentration that day was on me, eying my every move. Every so often he nodded, as if he was beginning to understand what he was seeing. He said nothing. I found it hard to concentrate on my golf hits, bothered by what my father was concluding from watching me. Did he only see his pathetic son, or was he seeing a teen girl?

“You have a model swing, Perry,” dad said finally, after perhaps twenty hits. “Your coordination is decent and you’re graceful. I’m sure we’ll get more power out of your swings if we work at it.”

After nearly an hour, my drives did begin to go further, never as far as the girl several tees away, but many were going beyond the 150-yard sign, bringing smiles of encouragement from dad. I found myself enjoying myself. When I finally got one nearly to the 200-yard sign, the girl yelled out, “Good shot.”

I waved back at her and she smiled.

My dad watched this exchange and a broad grin crossed his face. His response bothered me since he probably thought there might be some male urges in me; perhaps he saw a budding romance between his son (me) and the lovely girl. Little did he know that my interest in her was in the cute skirt she wore; I wanted one just like it.

It was on the drive home that dad finally mentioned my announcement that I wanted to be a girl. “I’m not happy about all this, Perry. You’re a boy and I hope you’ll grow up to be a man,” he said.

“I’m sorry, dad,” I said.

“Well, if what mom says is true that it’s in your nature to be female, then we’ll have to see. I love you, son, and always will.”

“Thanks, dad. I love you too and don’t want to hurt you.”

We stopped at a red light, he turned to me and smiled, “Well, as you saw today, fathers and daughters can golf together, too.”

*****
Later that day, Cindy and Perry suspended their “Ask Perry and Cindy” website with a brief announcement that would appear whenever anyone sought out their site:

“We are sorry to announce that we have suspended this website. It became apparent that as two high school students, we were unable to continue with the growing demands of the site and successfully continue our schoolwork.

“Both of us underestimated that the site would become so popular, and we received far more inquiries than we could possibly and conscientiously handle. We hope the site has been of service to all our teenage readers and apologize to any of those who feel we have disappointed them.

“For those interested in continuing to meet and share experiences, we invite you to our Facebook site. We will no longer be offering advice and handling queries, but all of you are welcome to network with each other there.

“Happy teen years to all. We love you all.

“Cindy and Perry”

Cindy and I cried as we wrote these last words. Even in this farewell message, we were not being totally truthful. Yes, our schoolwork had suffered due to the time involved in the website and, yes, the demand was overwhelming. The real reason was that I no longer wanted to be living a lie; I felt I had been dishonest and duplicitous in letting everyone assume I was a lovely teen girl, even if I felt like one.

“I feel I have been living a lie, Cindy, once I realized that everyone thought I was a girl and that I did nothing to change that,” I told Cindy that afternoon.

“Are you sure you’re not a girl, Perry? I don’t think it was a lie,” Cindy said.

“You know what I mean, and look what I did to a sweet boy like Jamie. He fell in love with a pretty girl. But I’m not a girl. I was so cruel to him, leading him on like that.”

Cindy hugged me. She knew how devastated I was after the conversation with Jamie. I may not be a girl, due to that ugly extension between my legs, but I knew I was acting like a girl in my sorrow over losing Jamie. In the end, Cindy agreed to end the website, realizing that I had become uncomfortable with continuing a deception.

*****
Several days later, I was cornered by Melanie Scouter, a girl in my Social Studies class; several of her friends joined her in confronting me as I left the class, on the way to my Chemistry class.

“Why did you and Cindy close the site?” she demanded.

“Yeah, we loved it,” echoed one of her friends.

“Thanks,” I said. “But as we said, it got too much.”

“Perry, I loved your comments,” Melanie said. “It’s just like you were a real girl.”

“Yes, you seemed to know what I was feeling. Like you’re just one of us girls, Perry,” said her friend.

I began to blush. I nodded, and started to head off down the hall, but Melanie stopped me and dragged me into an alcove where she and I could talk without being overheard.

“I got to tell you that some of the boys were going to blow the whistle on you and announce online that the Perry on that site was really a boy,” Melanie said.

“Oh. I was afraid that might happen, but I really didn’t plan on being taken for a girl,” I argued. “They just assumed it, I guess.”

“Well, I always thought Perry was a girl’s name anyway,” she said. “And really, your discussions were so girly.”

“I just tried to understand how all of you felt so I could answer the best I could.”

“We all loved it, Perry. Really.”

“I gotta get to my class. Thanks Melanie.”

“I hope we can be friends, Perry,” she said, giving me a quick, surprisingly passionate kiss on my lips, before turning and walking quickly down the hall.

*****
“Do you think you’d like to live your future out as a girl and then a woman?”

Dr. James Aliopolous asked that question no more than ten minutes into his first interview with me. I paused before answering, looking at the dark-complexioned, handsome man in front of me. I knew my answer would be critical; Dr. Aliopolous was a renowned psychiatrist with a reputation in dealing with gender dysphoria and his diagnosis would be an important determinant as to whether I might enter into transition from male to female.

“Just take your time, Perry. Tell me your real feelings, not what you think I’d like to hear, or what your mother might like to hear. Besides, she’s not here. It’s just you and me.”

I nodded, still reluctant to answer. In truth, while I had adopted so many feminine traits and loved dressing as girlishly as possible, I had never seriously considering changing my gender. I just thought I was doomed to live as a sissyish boy and man. Often, I had wondered if I might be gay and, of course, I was often accused of that. What else do you make of terms like “faggot,” “queer,” “nancy boy,” and “Mary?” But that didn’t seem right to me; the idea of boy-to-boy loving was hardly attractive.

“Doctor,” I started out slowly. “I don’t really know yet. I know I love being with girls and wearing girl things. And I had an online boyfriend for a while, and I dreamed that I was his girlfriend. He was such a sweet boy.”

The doctor nodded.

“Are you and he no longer in contact?”

“No,” I shook my head sadly. I felt I was going to cry.

“Here,” Dr. Aliopolous said, handing me a tissue from a box on his desk. He smiled, obviously seeing my truly feminine reaction to the mention of this online boyfriend.

He continued the consultation until my 50-minute appointment was up. He ended without saying anything about his diagnosis, saying only that we’d need another session. He made one suggestion: make up a list in two columns, headed “Pro” and “Con” in considering whether I’d like to transition to female.

“Maybe the list will help you,” he said, smiling. “You can keep the list to yourself, or share it with me at the next visit. It might help you.”

*****
“Mom, when he asked me if I really wanted to be a girl, I was afraid to answer ‘Yes,’” I said as mother drove me home from Dr. Aliopolous’ office.

Mother didn’t say anything, seemingly concentrating on negotiating our city’s modest rush hour traffic jams as we continued down Lincoln Avenue.

“Mom, why couldn’t I say ‘Yes’ to him?”

“Maybe, you’re not convinced that you should change, darling,” she said. “It’s a big step.”

“But, mom, I’m a girl. I know it.” My voice cracked as I said the words. I envisioned myself in the arms of Jamie, being caressed as his girl and feeling warm and protected. How often images of Jamie popped into my head!

“That’s your decision, honey. Whatever you decide, you know I’ll love you either way.”

“He asked me to list the ‘pros’ and ‘cons’ of transitioning before I see him next week.”

“Do you want me to help you with that, Perry?”

“No mom, he told me to do it by myself. Thanks anyway.”

“He sounds like a good psychiatrist,” she said, quickly changing the subject. “Now, you’ve had a big day. What would you like to do for dinner tonight? We could stop at La Coquette for a nice dinner, or do pizza or go home and see what we got in the fridge. What you think?”

“Let’s just go home, mom,” I said. I was eager to get comfortable; I had a new nightgown and robe combo and I wanted to wash my hair. And I was eager to begin my list.

*****
Creating this list was more difficult than I thought it would be. At first, I just wrote “Pro” and “Con” at the top of a sheet of school notebook paper and tried to list the various items on each side of the question. I thought I’d try listing all the reasons why I didn’t want to become a girl.

“I’ll be teased and harassed,” I wrote. The moment I put those words down, I realized that I’m being teased and harassed now; I was regularly laughed at or despised for my sissy mannerisms and feminine ways. So what’s the difference?

Then I wrote: “Trouble with my ID cards for school, etc.” That was an obstacle, I knew, but it’s just a hassle that usually can be overcome with time, but everyone has barriers like those. No big deal.

Also: “Dad will be disappointed.” Yes, he had said he wanted me to become a man, but didn’t he also say that “fathers and daughters golf together?”

Then: “Grandma and grandpa won’t like me anymore.” That gave me pause; they have yet to see me as a girl. I know that grandpa as a young man played baseball, even reaching the higher minor leagues; now he coached in a youth league. I know he wasn’t happy that I had never been able to throw a baseball as far as most boys, but apparently I had developed good form; he said I had a nice swing at the plate, even though most of my hits were pretty weak. Grandpa was a sweet man who had patience when we played catch. Never once did he say, “You throw like a girl,” which I probably did at first. Maybe he and grandma would understand, I began to think. After all, I was sure they wanted me to be happy.

My next entry was more troubling: “No one will want to be my life partner.” This really bothered me, since I had done enough research online to learn that many transwomen had been unable to find a man who’d accept them, even if they had had sexual reassignment surgeries. And, I probably couldn’t find a lesbian partner, either. I’d be alone in the world.

“Oh my darling, Jamie,” I cried out, tears rolling into my eyes. He was gone from my life; how heavenly it had been to have been his girlfriend, and now we’d never see each other.

I gave up on the “pro-con” list and flung myself onto my bed, crying myself to sleep, dreaming I was dancing a Strauss waltz in a lovely gown with a handsome, young Army officer in formal uniform as my escort. Of course, the young officer was my dearest Jamie.

It was 2:46 in the morning on the clock radio next to my bed. I sat up, rubbing the sleep from my eyes. The light on my desk was still on and the paper with penciled list of the “pros” and “cons.” I scowled at the list.

I got up, walked slowly to the desk and sat down. I took the pencil in my hand and in huge letters, all capitals, I wrote: I AM A GIRL!