The Road Not Taken

So there he remained, a confirmed old bachelor, and after he built his dream house overlooking the Gulf of Mexico, my wife and I visited him occasionally after the girls went off to college. He was always a delightful host, and he seemed blissfully happy living the single life. Then my wife was diagnosed with stage 4 glioblastoma, and he raced to Chicago to offer his support. But there was nothing that he - or the doctors at Northwestern - could do, and he flew back to Florida with a heavy heart.

Now she was gone, and it didn't take much encouragement from Tommy for me to decide to start living again. But after the events of the past 24 hours, how I was going to spend the rest of my life was the question. Did I want to live out my days as Gene, or start down the road less traveled?

* * *

The following morning, after I dressed myself in a wool skirt, sweater and tights, I brushed out my wig (I'd shampooed it the night before, as I'd done near the end for my wife when it became too difficult for her) and put it back on along with a bit of makeup. All seemed right with the world as I fixed myself a bowl of cereal and contemplated the busy day ahead, a day of deliberation, decisions and doubts...

My deliberations didn't last for long. I decided to pack an extra suitcase for Jeanne, my female alter ego. Gene resisted at first, but Jeanne was very persistent. In the end I decided to drive to Florida as Gene, meet up with Tommy that way, and play the rest of the weekend by ear.

My decisions centered around what to pack! I quickly discovered that it's much more challenging for a woman: first she has to decide what outfits she's going to wear (an Internet search confirmed that the weather was going to be sunny in the 60's, although cooling off at night) and once she selects her skirts and dresses, she has to pack a matching purse and shoes to go with them, not to mention accessories and jewelry, then there's lingerie and hosiery (although I probably wouldn't need anything on my legs in Florida) plus something to sleep in, and last but not least there was all the makeup, moisturizer, brushes, etc. that a woman needs, oh and don't forget your wig! A sweater coat was the final addition to my trousseau.

After I carefully crammed everything into one of my wife's old suitcases, I spent the rest of the day fighting off doubts about whether I shouldn't just leave the extra suitcase at home and forget all about Jeanne for a while. But now that the Jeanne was out of the bottle, she wasn't about to go back in! So I packed a second overnight bag for Gene, tossed them both into the trunk of my Audi, and spent a restless night trying to make sense of what was happening to me before I finally fell asleep.

* * *

I was up well before dawn. Fortunately, the crack Chicago sanitation crews had plowed out the streets overnight, and after I blasted my Audi through the snow covering my short driveway, I was on my way to Dixie. You can imagine the jumble of crazy thoughts and emotions that tangled up my brain as I rolled towards my destiny...why in the world would I even consider exposing Tommy to my suddenly secret self? He'd probably laugh me out of town! No, Tommy would never do that, he'd probably just write me off as a nutcase who went off the deep end when he lost his wife, and was pathetically trying to hang on to her by dressing up in her clothes. Is that was I was becoming, some kind of psycho?

And why the fuck would I even consider trading my life for that of a woman, with all of the shit they have to put up with? This thought occurred to me each time I pulled off the Interstate and found a country road so I could relieve myself. If I were a woman, I'd have to expose myself to the pandemic in a filthy gas station restroom, yuck!

But then I remembered how it felt to dress myself in that soft, forbidden clothing, and how much younger I looked when I put on my wig. Crossdressing must be some kind of fountain of youth! I hadn't had orgasms that strong in decades. Just thinking about it made me start to get hard downstairs, and I fumbled with the radio dial until I found a college football game to take my mind off of girlish things.

I drove straight down through Indiana, Kentucky, Tennessee, and Alabama. By then, the weather was springlike, and I opened my sunroof and drank in the warm southern air. I left the Interstate just before the Florida state line, skirted the honky tonk scene around Destin, and pulled up in front of Tommy's three story beach house just before sunset. We greeted each other with bear hugs - the pandemic be damned! - and after I dropped Gene's suitcase in the guest room (Jeanne's suitcase stayed in the trunk) we sat down on wicker rockers on the deck overlooking the Gulf, popped a couple of Land Sharks, and watched the glorious sunset turn into a spectacular green flash.

Tommy fired up the grill, and over delicious swordfish and a sublime bottle of Pino Grigio, we caught up on lost times. We talked a lot about my wife at first, not the way she died, but the happy days when we were all young. Gradually the conversation drifted back to our boyhood, growing up as next door neighbors in a leafy Chicago suburb. After a couple of beers and two glasses of wine, my inhibitions were slipping, and Jeanne made her move. "Do you remember that Halloween when you dressed up as a girl?" I asked him.

"Sure, that was a long time ago." He had a quizzical look on his face. "What brought that up?"

"I remember how my mother kept going on about how adorable you looked, and she begged me to try it myself the next year...."

"Well, you should have. You would have been a knockout."

"I know. Tommy, do you mind if I ask you a personal question?"

"After all these years? Of course not."

"Did you ever come close to getting married? I remember when you were in high school and college you had to beat the girls off with a stick."

He laughed out loud. "No Gene, I wasn't lucky like you. Never found the right girl."

"Did you ever fool around with guys?"

This question floored him, and he was silent for a long time. "Why would you even think such a thing?"

"I don't know...you were always ahead of your time, and now in this day and age, guys hooking up are no big deal."

He shook his head. "Maybe you've forgotten, but when we hit the dating scene, HIV and AIDS were running wild, and that kind of shit could be deadly. Are you trying to tell me you think I'm gay?"

"No Tommy, I never really suspected that, not for a minute. This has more to do with me than it does with you."

"What the fuck are you talking about?"

"When we were little kids, a few years before that Halloween, I dressed myself up in my sister's clothes one time."

"So what? Do you think that makes you gay? You were married for thirty years and had two kids, for God's sake."

"Yes. Tommy, the other night, I tried on my wife's clothes."

"You what?"

"I know, you must think I sound like a lunatic. Maybe I am...." I started to cry.

Tommy was silent for what seemed like an eternity. "That's quite a confession. All right, here's one of my own, since we're being silly. I always wished you were a girl."

"You what?"

"All those years, palling around with you, I wished you were a girl so we could get married. Of course, we were only children...." his voice trailed off.

My heart jumped. "You wished I was a girl?"

"Sick, huh? Gee, do you think that's why I never settled down?" he asked sarcastically.

"I don't know what I think right now, Tommy. On second thought, I know exactly what I think. I think I want to try living as a woman."

This totally floored him. "Wow," he said at length. "Just like that. What about your children, and your grandchildren?"

"I don't know, maybe I can be like a chameleon, and go back to being Gene when I see them. I know I must sound totally screwed up. It's just that, when I started dressing up again, it was like somebody threw a switch or something. It just felt so right."

We sat and stared at each other for a long time. "So what does your better half call herself?" he finally asked.

"Jeanne, my name is Jeanne," I said, pronouncing it like the genie I'd just let out of the bottle, using the, soft sweet voice that I'd been practicing for hours in the car.

"And what does Miss Jeanne look like?"

"Would you like to meet her?"

"Sure, why the hell not."

"Give her half an hour," I said as I sprinted for my car to fetch Jeanne's suitcase.

* * *

I was beyond excited when I tore open my suitcase and tried to decide what to wear. Decisions, decisions...finally I selected a white eyelet skirt, a black and white top, and matching flats. I also dug out a bra and panties, along with my wig and makeup bag. After I tore off Gene's clothes and took a quick shower, I gave my face a close shave, smoothed on some moisturizer and started in on my makeup. Foundation, eye liner and shadow, a touch of mascara, a smidge of blush and a touch of lipgloss all went on easily, and after I brushed out my wig it fell softly around my neck. The bra I'd packed was one of my wife's old wonder-bras, which gave me a hint of cleavage, and my panties slipped on like I'd been wearing them all my life. I took a few moments to catch my breath while I put a quick coat of polish on my nails. After they were dry, I stepped into my skirt - it was fully lined, so no slip this time, I was learning fast - and pulled my top over my head. I put on some jewelry, zapped myself with cologne, stepped into my flats, and I was ready to face my future.

I heard a blender working in the kitchen, where Tommy putting salt on the rims of two margarita glasses. I tiptoed up to him and asked, "Do I pass inspection?"

He spun around and nearly dropped the pitcher of margaritas. "Holy shit, is that really you?"

"None other. What were you expecting?"

He shook his head. "I can't believe it. You look one hundred percent female. And you're not bad looking," he added, shaking his head.

"Why thank you, kind sir. Can the not-bad-looking-lady help with the margaritas?"

"They're done," he said, handing me mine. "Well, here's to my new lady friend." We clinked glasses and studied each other over the rims while we sipped.

I followed Tommy into the living room and we sat down awkwardly on the sofa. "I didn't really mean that," he finally said.

Uh oh. "You mean I don't really pass as a woman?" I was crushed

"No, silly, the bit about you're not looking bad. You look fantastic, Jeanne, beyond my wildest expectations."

I fluffed my skirt and crossed my legs at the ankles. "I must admit, this has been a pretty amazing trip for me. I have one more confession for you, Tommy."

"Oh?" He cocked an eyebrow.

"Back when you were wishing that I was a girl, I had a little crush on you. Not that I was gay or anything...."

"Now you tell me! I think it's time to cut the bullshit. Of course I'm gay. I'm ridiculously selective, but I've had my share of lovers over the years. Not in a long time, though."

I was shocked but not surprised. So my wife had been right about Tommy! Well, of course she was, weren't women always? "Do you ever think about what might have been, between us I mean?" I asked him.

"How could I? You married the most wonderful woman I've ever met. I was insanely jealous of her, but you always seemed untouchable."

I reached over and took his hand in mine. "I'm not untouchable any more, Tommy."

He took me in his arms and hugged me. I looked up into his eyes and gave him a little kiss on the lips. He pulled back for a moment, then responded with a lover's kiss that penetrated deep inside my soul, curling my toes and taking my breath away. We remained locked in a lovers' embrace as we held that kiss for what seemed an eternity. When we finally came up for air, my head was swimming in confused happiness. "Can I ask you one question?"

"Anything," he smiled as he kissed my forehead

"If you're gay, how can you be attracted to me if I look like a woman?"

He reached under my skirt and squeezed my panties. "Promise you won't change anything. I love you just the way you are."