The Road Not Taken

(c) 2020 by Thrillerauthor

For the first Thanksgiving in almost thirty years, I was alone. My beloved wife had passed away in late September after a long, losing battle with cancer, and by the time she died even she'd come to agree that the end of her struggle would be a blessing, which it was. Our two grown daughters, and our growing flock of grandchildren, all lived halfway across the country, and since our church was unable to schedule a proper funeral thanks to the ongoing pandemic raging across America, I'd assured them that they could say their goodbyes via Zoom and FaceTime, spare themselves the risk of getting on airplanes, and leave the burial arrangements to me.

Now that she was gone, I had to face the reality that until a vaccine for the dreaded Coronavirus was perfected and distributed, I'd be going through life alone. Both of the girls extended halfhearted invitations to come for Thanksgiving, but we all knew that the dangers of contagion in an airport, or a highway gas station, made that extremely problematic for me, and both seemed relieved when I assured them that losing their other parent was not what they needed, and that I'd be just fine on my own for a while.

Fortunately, my wife and I had lived modestly on my six figure income, and after our daughters got married and moved away, we'd sold our rambling Tudor in Winnetka and settled into a comfortable townhouse near Lincoln Park. We'd enjoyed a few good years taking in all of the attractions that Chicago has to offer until the day of her diagnosis, but the last few months had been a nightmare, and I hadn't found the energy to begin clearing her things out of our closets and dressers in order that I might begin making a new life for myself.

So that was how I intended to spend my Thanksgiving. I'd semi-retired when the demands of her illness became overwhelming, although part-time consulting via the phone and the Internet still provided a tidy income, and it was time that I confronted the practical realities of single life.

The first steps would be the hardest: every time I entered our large walk-in closet, and saw her skirts, shoes and dresses neatly arrayed on "her half" I almost came to tears. Selecting her burial outfit had been torture for me, and I knew that going through her things, picking out the few heirlooms and pieces of expensive jewelry that the girls might want, and bundling up the rest to give to charity was going to be sheer agony.

Or so I believed....

* * *

Here I must digress and take you back into the recesses of my memory, in particular to that tender time just before the onset of puberty when boys and girls are still very much alike. I was a pretty boy, and I was told more than once by female relatives that I would have made a very pretty girl...I had an older sister who was an incorrigible tomboy, far more gifted athletically than I was, and she used to tease me mercilessly that she should have been the boy and I should have been the girl. Of course, once she got to high school, she discovered boys, and I watched in fascination as she blossomed into a beautiful, feminine young woman.

After she left for college, I was still an awkward tween when my parents left me alone for the first time so they could attend my father's twenty-fifth reunion at the Ivy League college he went to back east. I'll never know the reason why, but as soon as they left, I was drawn to my sister's bedroom like a moth to a flame. Almost mechanically, I began sifting through her drawers and pawing through her closet, until I'd laid out on her bed everything I thought a girl would need, from lingerie and pantyhose to skirt and top, along with a pair of flats and some bling from her jewel box. My facial hair was still nonexistent, and the hair on my head was just long enough to pull back into a ponytail, so after I fastened it with one of her scrunchies I started to teach myself how to dress like a girl.

The cotton panties were no big deal, nor was the bra that I fastened backwards and stuffed with tissues after I'd spun it around. It wasn't until I sat down on her bed and started to tug on her pantyhose that I experienced a sensation previously unknown to me, a strange and wonderful feeling from my toes to my tummy, as the silky stockings slid up my hairless legs. I was transfixed by the sight of them, my legs, suddenly transformed into a girl's legs, as pretty as any I'd ever seen on a girl, only now a part of me as I finished pulling the pantyhose up over my panties to my girlish waist. Almost in a trance, I fumbled with the next item in my pile, a satiny slip, which made me shiver as I dropped it over my head.

After putting on my lingerie, getting myself into a skirt and clingy top was almost an anticlimax. The skirt slid up over my slip, and I had to twist it around to zip it up before I straightened it out. Putting on the top was just like getting dressed as a guy, except for the twin bulges in front. My stockinged feet slipped easily into a pair of my sister's weejuns, and after I fussed with one of her necklaces and clipped on an old watch of hers, I walked over to her full length mirror and contemplated what had become of me. Gone was the callow youth, replaced by an attractive coed. And I was attractive! My female relatives had been right: I made a very pretty girl, although something was missing...I spotted my sister's makeup stash on a corner of her dresser, and although I didn't have the confidence to try anything with my eyes, her lip gloss was easy to apply, and when I was finished, my transformation was complete. I was a girl.

I stayed that way most of the weekend. That evening, as I started to get used to the feeling of wearing a skirt and nylons, I puttered around the house, warmed up one of the dinners my mom had left for me (I tied one of her aprons over my skirt to protect it) kicked off my shoes and curled up on the sofa to watch TV. All the while, the strange, wonderful sensation in my panties continued to glow, although I was a bit too young to approach a climax. I slept in one of my sister's nightgowns, and the next day (Saturday) I put on a little fashion show for myself: I bounced around the house in her old cheerleader uniform, did my homework in a kilt and knee sox, and that evening I treated myself to another warmed-up dinner in a dress, heels and stockings. I even brushed out my hair into a feminine style and complemented my lip gloss with a touch of eyeliner and mascara.

The next morning, I was up early, and although I was tempted to prolong my vacation from reality, caution got the better of me, and I spent hours laundering and ironing the clothes I'd worn, putting everything carefully away, and scrubbing the last vestiges of makeup off my face. By the time my parents returned that afternoon, there was no trace of the girl that I'd become, although my memories of those fantastic feelings in my panties lingered for a long, long time....

* * *

Now, as I contemplated the task of clearing out my wife's clothing, memories of that forbidden weekend came flooding back once more. I'd often thought about those magical moments, but as soon as I hit puberty, and my bones and body hair started to grew, I knew that I could never recapture the magic. Then I discovered girls, and my weekend as one of them was almost forgotten.

I sowed my share of wild outs in high school and college, but once I met my future wife sophomore year, it was love at first sight, and we were married a week after graduation. The first of our two daughters quickly followed, we settled down into domestic bliss, and the next thirty years flew by, until the cruel hand of fate turned me into a widower. Now, as I started in on her closet, it occurred to me that for the first time since that long-ago weekend, I had the opportunity to secretly transform myself into a female once again. Although I'd grown into manhood, I was relatively short and slim, and I was pretty sure that I could easily fit into my wife's wardrobe. When she started on chemo, she'd gotten an expensive wig, and I was certain that would fit me too.

The question was, did I really want to take another trip down that long forgotten road? Over the intervening years, as trans kids emerged from the shadows into the national discourse, I'd occasionally wondered what might have been if I'd been born into today's world...would I have been tempted to continue with the exploration of my feminine side? I'd always dismissed the very notion as absurd: why would a successful, happily married man trade his status as a husband, father and grandfather for the scorn and ridicule that a trans woman has to deal with every day of her life?

But now, things were different. I'd made all the money I would ever need, my childrearing days were behind me, and the love of my life had been taken away from me. So what if I decided to try on some of her old clothes before I gave them away? Believe it or not, my greatest concern was that she might look down on me from Heaven and be shocked and appalled to discover that her husband was really a pervert!

Eventually, curiosity won out over fear, and on a snowy morning the day before Thanksgiving I took my first fateful steps down the road not taken.

There was no way I was going to leave my townhouse dressed as a woman, so seasonal fashions were beside the point - after months of self-imposed isolation and despair, what I desperately yearned for was a trace of those long-ago feelings of joy and contentment, anything to take my mind off the sadness and loneliness of my current existence. So I stepped into the closet and emerged with a simple skirt and top, similar to the ones I'd first tried on so many years ago, along with a pair of my wife's favorite flats. They always made her largish feet look very cute, I remembered sadly before I started opening her dresser drawers and pulling out lingerie and pantyhose.

Then it was off to the bathroom, where I filled the oversized tub with a mountain of my wife's favorite bubble bath. Descending into the suds with shaving cream and razor in hand, I spent the next hour giving my face a close shave and tediously removing all of the hair on my chest, arms and legs. I've never been particularly hairy to begin with, although I made a mental note that if I was ever going to get serious about this, I'd need a long-handled mangroomer to take care of my back...what was I thinking? Surely this was a one-shot deal, a few brief moments of escape from my lonely life before I returned to the real world and donated all of my wife's things to charity.

After I dried myself off, I decided to try on her wig before I went any farther. If it didn't fit, or if I looked ridiculous, that would bring a quick end to my foolish fantasy. But it did fit, perfectly, a cute bob with stylish bangs, and since my own thinning hair had gone almost gray, I immediately looked years younger. Not quite believing I was doing it, I returned to the bedroom and stepped into a pair of her silky panties - because I had a man's hips, they fit just fine - and for the first time in over forty years, I struggled with the mechanics of a brassiere again, finally resorting to the same technique I'd employed as a boy before centering it on my chest and stuffing the cups with wads of tissues.

I'd almost forgotten how delicious nylons felt on my legs, but the old memories came flooding back in a hurry as I slowly eased the delicate hosiery up and over my knees, one foot at a time, reveling in the sensation when they were finally snuggled into place. I didn't need to look at the bulge in my panties to realize that those wondrous feelings bordering on ecstasy so many decades ago had matured into a strange eroticism, and after all the long months of abstinence, my penis erupted without warning into a raging orgasm, as intense as anything I'd ever experienced, and I fell to my knees in shame until the pulsing slowly subsided...what must my wife, looking down on me from Heaven, think of me now?

I shook with sobs as I lay there on the bedroom carpet, until my feelings of self-loathing were gradually replaced by a strange kind of contentment. It wasn't the usual post-orgasmic bliss, rather it was more a sense of serenity, as if I'd been liberated from all the burdens and heartache that had plagued me since the onset of my wife's illness. If she was looking down on me from Heaven - if there really was such a place -- then surely she'd be blessed with perfect understanding, and she would already know that her husband had been possessed with a dual nature, and that he had subconsciously sublimated the female half of his personality to her happiness throughout their marriage. Now that she was no longer with him, he could either seek out another woman to take her place, or allow his own inner woman to break free.

The icky mess in my panties broke this bizarre chain of thought, so I got back on my feet and peeled them off along with my stockings. After I wiped myself down, I selected another pair along with some fresh pantyhose, and my exhausted penis behaved itself this time. I was still feeling somewhat bewildered, and after I slipped into a slip I returned to the bathroom to experiment with my wife's makeup. It was all still there, just as she'd left it before her final trip to the hospital, and I again experienced feelings of shame as I gingerly began to experiment. I'd watched her doing this at her vanity countless times, and I was surprised by how easily I was able to create a more feminine face. I also filed and polished my fingernails, and as I sat on her tuffet in a slip and nylons, I could feel that sensation welling up again deep inside me. This time, I tugged down my panties and hose and stared at my reflection in the mirror while I stroked my stiffening penis past the point of no return, until once again my body surrendered to a shattering orgasm which was even more intense than the last one. I hadn't had two orgasms in rapid succession like that since my honeymoon!

By now I was feeling quite languid as I pulled myself back together - my penis tucked back easily between my legs this time - and I returned to the bedroom to try on my wife's skirt and top. Both fit me perfectly, and after I squeezed my feet into a pair of cute flats, I fussed with some her old jewelry before I finished myself off with a spritz of her favorite cologne, which brought a little tear to my eye.

When my transformation was complete, I sat down on an ottoman and stared at my reflection in the mirror over her dresser for a long, long time. For the first time since she'd been diagnosed with cancer, I allowed myself to smile....

* * *

That evening, I fixed myself onion soup and steak frites for dinner - I'd become quite adept at cooking for myself during my wife's long illness - and, just like that first time so many years ago, I kicked off my flats, curled up on the sofa, and had my supper with the evening news, only this time there was a lovely bottle of Pinot Noir to accompany my meal. By the time Tom Skilling finished his forecast, which called for heavy snow all night, I was slightly blitzed. The next day, I'd have to turn myself back into Grandpa for my Zoom and FaceTime calls with my daughters and their families, but tonight I was feeling playful, so after I cut myself a piece of chocolate cake to go with the last of my red wine, I decided to call Tommy, my oldest and dearest friend.

Now Tommy and I had been best friends since third grade, and he'd been the best man at my wedding. Tommy had a spectacular career working for the Pritzkers before he retired early to a beachfront villa on the Florida panhandle, also known as the "Redneck Riviera" which had the closest ocean beaches to Chicago, a long day's drive away.

Tommy never married, and my wife had always suspected that he was gay. But you could never be sure with Tommy, who was larger than life with an effervescent personality. He'd become very close to my wife, and he'd been devastated when she finally passed away. I'd received a text from him earlier that day: "r u ok call anytime" which was his way letting me know that he would always be there for me. I picked up my cellphone and punched in his number.

"Hi guy" he answered.

"Hi Tommy. Thought you could give me some tips on Thanksgiving for one."

Part of our relationship was based on teasing each other unmercifully no matter how taboo the subject, and he responded in kind. "My specialty. Have you considered working in a soup kitchen?"

"After the pandemic. Seriously, how have you been?"

"Just another day in paradise." Tommy had a lovely beachfront villa on a tony stretch along 30A, and he delighted in ridiculing me about the Chicago weather. "Why don't you come down here and warm up for a few days?"

That sounded tempting. "That sounds tempting."

"So get your ass down here."

I glanced out the window at the steady snowfall. "Right now I'm snowed in."

"So what else is new? Seriously, once you get plowed out, point that Audi south and thaw yourself out. You could use a change of scene, Gene."

I glanced down at my silky legs. If he only knew! "Maybe you're right...."

"Of course I'm right! Have yourself a merry little Thanksgiving tomorrow, let your blizzard blow over, and come on down. I'm serious, this will be the best thing for you."

For reasons which will become clear later, I accepted his invitation, and we made plans for me to arrive on Saturday.

* * *

I slept for 12 hours in one of my wife's Lanz nightgowns. Thanksgiving morning, after a light breakfast still dressed as a woman, I reluctantly changed back into Grandpa and put on a show for my older daughter and her family via Zoom. Yes, Grandpa was doing just fine. Yes, I missed Grandma terribly, and I was sure they did too. My dinner would be a complete Thanksgiving feast with all the trimmings, courtesy of a famous Chicago restaurant and Uber Eats. I love you all and hope we can get together soon. No need to mention that I was getting away to Florida for a little "me time" with an old friend. The FaceTime call with my younger daughter and her family went down along similar lines.

I waited until after the Uber driver delivered my feast before I put everything in the oven to keep it warm, stripped off my Grandpa clothes, and treated myself to a long, lovely bubble bath. Then I put on my wig and makeup, selected one of my wife's favorite dresses from the closet, and slowly dressed myself, with heels and stockings, for Thanksgiving dinner. I set the dining room table, lit some candles, opened an expensive bottle of Chardonnay and picked at my lonely dinner, watching the world fill up with snow as I looked back on all the wonderful Thanksgivings that I'd shared with my wife, and looked forward to my upcoming weekend in the Florida sun with Tommy.

I will now confess that I always had a secret boycrush on him. Nothing ever came of it, of course, and we both dated dozens of pretty girls all through high school and college. When I got engaged, he personally took charge of the wedding arrangements - as much as my bemused fiancé and her exasperated parents would let him - and throughout our married life, he remained extremely close to us. Our daughters both adored him - he was Godfather to both girls - and we occasionally invited him to join us on holidays. "Party of five," I remember him telling the startled maitre d at an exclusive Chicago restaurant, "one lovely couple, their two darling daughters, and me - the fifth wheel."

But he never married, nor even came close as far as we could tell. True, the Pritzkers were very demanding to work for, and he traveled throughout the world constantly, trouble-shooting for their expanding empire of Hyatt hotels. By the time he retired early to Florida - his elderly mother was in a nursing home there, and he wanted to be near her - we'd given up hope that "Uncle Tommy" as our daughters called him would ever tie the knot.