What If I Had Taken That Other Road?

The Road Not Taken is a poem by Robert Frost, published in 1916 as the first poem in the collection Mountain Interval. Frost said that this poem was “tricky” and often misinterpreted. While many readers take it to refer to the importance of not following the crowd, Frost said that it referred instead to the tendency to regret past decisions, even inconsequential ones.

Two roads diverged in a yellow wood,

And sorry I could not travel both

And be one traveler, long I stood

And looked down one as far as I could

To where it bent in the undergrowth;

Then took the other, as just as fair,

And having perhaps the better claim,

Because it was grassy and wanted wear;

Though as for that the passing there

Had worn them really about the same,

And both that morning equally lay

In leaves no step had trodden black.

Oh, I kept the first for another day!

Yet knowing how way leads on to way,

I doubted if I should ever come back.

I shall be telling this with a sigh

Somewhere ages and ages hence:

Two roads diverged in a wood, and I—

I took the one less traveled by,

And that has made all the difference.

The day of my 14th birthday I became a big fan of Robert Frost. Until the day before my 14th birthday I do not think I had ever heard of Robert Frost. Then he was chosen by incoming president John F Kennedy to read a poem during the inauguration ceremony. The next day I scoured the school library for books on Frost and his poetry. His love of nature struck a large chord with me. His messages within also resonated, none more so than The Road Not Taken wherein he predicts that sometime in the future he will be looking back and perhaps wondering what would have been if he had made the other choice. That poem was written in 1915 and Robert Frost lived to the 1970s, plenty of time to look back and wonder.

Just like Frost predicted for himself I have recently been looking back and wondering about my own roads not taken. Possibly you have found yourself doing the same.

Let me give you an example of where these reflections are taking me. Less than 10 years after my introduction to the works of Robert Frost I was a graduate of one Canadian university and doing post graduate study in my specialty at a university in Toronto, Canada. My wife and baby had joined me as we occupied a modest apartment on the west side of Toronto’s bustling downtown. The school year ended and my wife decided to take the baby, by then a toddler back to live with her parents while I worked part time in a restaurant and readied myself for advanced studies during the hot summer in Toronto. So that is one ‘road not taken,’ What if I had delayed my studies and gone with my wife to her parents. Would our relationship have been stronger? Would she have then not met the man who was to become the ‘love of her life’? But that is not the point of this story.

I’m an almost lifelong crossdresser. I get tremendous pleasure out of dressing and appearing as a female. I have a well-developed female identity and the wardrobe to go with it. A lot of what I have become I can trace back to that summer in Toronto. I look back at that summer and see there were several roads taken and not taken, most of those junctions I did not even recognize at the time. At several junctions I think the taking of a different road would have definitely altered the course of the rest of my life.

Here is a story I’m calling ‘Linda meets Linda: The summer of “68.” I can tell you that it starts out as a true story but at some point I diverge on to the ‘road not taken. Your task, if you should choose to read the story is to tell us where I might have diverged from the road taken.

I had written my last exam and that evening started my first shift at the downtown Toronto steak house restaurant where I would be working a mix of evening and overnight shifts until my summer school studies were to start. My wife soon tired of my work all night; sleep all day routine. She packed up our child, most of their clothes and headed to her parents’ place. That was fine with me. I liked the quiet and besides she had left behind enough lingerie for me to enjoy and satisfy my sexual needs. Yes, even before that fateful evening I had developed a love, almost a craving for bras, panties and slips; stockings and garter belts, too. I would have loved the rest too but for some reason while her lingerie fit her skirts and dresses did not.

My Friday evening shift at Lindy’s ended about 11 p.m.. The restaurant was still busy and I was pulling in great tips but I had been working since six, was tired and they had to give the overnight shift some of the after-theatre business. I was glad to step aside but too restless to go right home. This is my next example of a road not taken. I could have and perhaps should have headed to the subway and gone straight home. How different would my life have been if I had done that instead of walking up Yonge Street intent on checking out the Saturday evening action?

I soon came to the St. Charles Hotel. The St. Charles wasn’t really a hotel. They did not rent out rooms but at one time in Toronto to get a license to sell alcohol a tavern had to be called a hotel. I knew about the St. Charles. Today we would probably refer to it as a gay bar. Back then: well I don’t want to offend anyone by using a politically incorrect term. Let’s leave it at that.

The St. Charles had one front entrance but just inside there were three choices to make. Two were to rooms to either side each containing large horseshoe shaped bars and lots of men standing around. The third choice led up a flight of stairs to where I heard music playing. I could have gone in to either of the side rooms. By that point in my life I had some experience letting homosexual men ply me with favors before they put my penis in their mouths. I chose instead to head up the stairs. What if that night I had chosen left or right or even reversed back out the door and headed straight home?

Upstairs the music was being played by a DJ in a night club. A man was at the door collecting cover charges. He let me take a look inside. I liked what I saw. There were women, lots of women. There were more women than men. Surely even I would be able to find a dance partner. I paid my fee and headed to the bar to get a drink and scout the room.

I asked one girl to dance and she accepted. After a few dances and a little conversation she invited me to join her friends at a table. I accepted and we made introductions all round. I guess we must have had a good conversation I don’t remember. I do remember being the only male at the table and buying a round of drinks. I also remember dancing with one of the other girls who was introduced to me as Linda. Soon I had transferred all my attention to Linda. She was very pretty, slim and long-legged, wearing a camel hair mini skirt and matching bolero jacket. Her hair was awesome, long and blonde. It did not surprise me that she was a hairdresser / beautician.

But something was strange about that place. It took me a while to comment but I eventually said to Linda, ‘you know some of these girls look like guys.”

Her reply: “Honey, we’re all guys.”

Now I guess a lot of rubes like me would have bolted for the door and that was probably another road not taken. I was surprised but not shocked. I was fascinated. I guess my experience as a transvestite and my experiences with male lovers conditioned me to want to find out more about Linda and her friends. We chatted and danced some more. We stayed together until closing time when Linda invited me to join her and her friends on a taxi ride to another friend’s apartment where the party could continue.

Another road not taken moment? Sure, I could have headed home. Instead the five of us piled in to a taxi and headed to I don’t know where. Naturally being the only guy I paid for the cab and we entered the apartment which was not so much an apartment but a rooming house with a common room where the party would be. The other gals congregated there where they would later be joined by another car load of gals. I learned everyone living in that house was either gay, or TG. Many of the gays did drag.

Instead of joining the gang Linda led me to someone’s room where we could have a more private conversation. I remember her telling me about how hard she was working so she could save up money for a sex change operation in Japan. No, that was not a pretense to ask me for money. I did not have to pay her then or ever after. Soon we were making love. She did not want to provide oral sex. We did kiss a lot and then she showed me how to enter her back door. That was a first for me, three firsts in fact. I learned how very slim girls like Linda could use a towel under their skirt to pad out the hips. I learned how to be gentle during anal penetration and I discovered the enjoyment in reaching around to hold her penis while we made love. That way I knew our climaxes were pretty well simultaneous.

You know what happens next: Another road not taken moment. With any other date I would likely have bolted for the door and that would have been the end of it. With Linda I lingered. We talked a bit more, got cleaned up and joined the other girls.

That is when things got really interesting.

I can’t wait for the next four weeks to pass when I can tell you the rest of the story. But I guess you can already guess what is going to happen next. . . .

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Tags: crossdressing, featured, Identity

Category: Transgender Body & Soul, Transgender Fun & Entertainment