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Part 2 of The Road Not Taken: Transformation

| Dec 11, 2017
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[Part 1]

As I get on in years I find myself looking back at the decision points in my life and wondering, as poet Robert Frost did about 100 years ago, about the roads not taken. Anyone who now drives relying on a GPS device for navigation knows that each day we have had many navigation decisions and just as many roads not taken. Now the GPS tells us which decision to make. When driving, the consequences of the decisions are usually small. However Frost’s poem is not about those. His roads are a metaphor for our important life decisions but I’m guessing you already know that.

I wonder how would my life have turned if I had chosen a different university, if I had not gone to that dance and met that girl, if I had withdrawn instead of gambling that she was not ovulating? How different would a person’s life be if 40 years ago he had chosen to do his studies in math and computer engineering instead of history and philosophy? Would certain world leaders have a different view of war if they had actually done military service and faced death head on?

That summer I spent in Toronto seemed for me to have been one road junction after another. Some small decisions ended up having large consequences for me. In my last article I reported that one night, as my restaurant shift ended, instead of heading straight home I wandered up the street and in to what turned out to be a gay bar. Upstairs was a small nightclub that turned out to be ground zero for Toronto’s drag scene. I met a gorgeous girl who turned out to be a guy and to make a long story short we had sex together.

Now the new part begins. As with last time, I will point to places where I might have taken a different road.


Note: My new friend’s name was Linda. It was some time later that I chose Linda as my femme name. It was not a coincidence. When Linda and I first met she called me Honey.

Linda and I started our recovery from sex. She excused herself to the bathroom, probably to wipe my semen from her behind. I used a bed sheet to wipe her semen from my hand. I was pulling up my pants when she returned to the room. She was silhouetted by the hall light. She was so slim with slim hips, slim chest, skinny legs and arms. Her penis was quite small. She had beautiful pale skin and lovely blonde hair which I couldn’t tell if it was a wig or her own hair. She was a hairstylist, after all. She was not the kind of guy I would normally hang around with. But at the same time she was different.

Then came another road junction. If Linda had been just another college girl in just another dorm room I would have been bolting pretty quickly with the term paper to finish or early class excuse. However as she dressed I became fascinated how the simple act of her putting on her padded bra and blouse, how she wrapped the towel around her hips and zipped up her skirt and how she easily slipped in to those heels could be turning me on again. Hey, I was a guy. I was supposed to be turned on by girls undressing, not dressing but it was what it was.

Linda suggested we rejoin the others who were still chatting in the common area. Instead of bolting for the door I agreed. We settled in together cuddling in an oversized chair with her sitting partly on my lap. It was not long before she could feel I was happy to have here there.

In the language of the era all the others present were she-males none quite as attractive as Linda but all comfortable in how they were dressed.

After a lot of kidding, a little drinking and a joint or two being passed around one of the girls suggested that I looked out of place and they should help me dress as they were. This might have been some kind of test. She might have been trying to draw out any prejudice in me or perhaps they knew that anyone like me who stuck around probably had a latent interest in his own dressing.

Being dressed up.

It was another ‘road not taken moment.’ I could have declined and headed for the door but instead without showing as much enthusiasm as I felt I agreed to give it a try. Linda and another friend took me back to the bedroom. They scrounged up a bra and panties, a mini-dress and wig. Linda tried to beat my penis in to submission but the erection just would not go away. So instead they settled for a panty girdle. They tried me in high heels but I was too wobbly for safety. They found a lower pair for me.

There was not much they could do with my make-up. They did their best with foundation to cover my facial hair but it had been growing for close to 20 hours by them. However they deftly added eye liner, mascara, eye shadow and lipstick.

If the panty and bra excited me sexually the dress, the wig and make-up fascinated me. I looked in the mirror and could not believe what was looking back. I tried to play it cool but I think Linda and her friends knew they had a live one here. We re-joined the others to much applause and some laughter. Someone took some photos of me and of all the girls together. The folks at the developing lab must have had some fun with that roll. I never got to see those photos.

Soon it was time to turn in. Linda and I made our way back to the same room. I think I would have been happy to wear a nightgown to bed but Linda gently insisted that she’d rather have a man in bed with her. I complied. We made love again, this time with less vigor. We finished without climax and fell asleep with me spooned up against her.

This may be pushing the limits of allowable smut on TGForum so I have left a lot for your imagination.

Despite the late night, Linda and I were up early. She was going to have a busy day at the salon and I did need to get home. She gave me her phone number suggesting we get together again. That created yet another ‘road not taken’ moment. It would not be the first time if I had said ‘I’ll call you’ and then discarded the number. That might have been my original intention. However on the subway and trolley bus ride back to the apartment I got to thinking what if Linda could help me and I could become one of those girls in the night club. I’d only do it part time and on weekends. I could still continue my studies. I could put it away at the end of the summer when I reunited with my family.

It still took me several days to call Linda. That is when I discovered she actually had a live-in partner who had been not too happy when Linda was out overnight. Nevertheless I got to talk with Linda and we discovered we both had the next Sunday and Monday off work. We made a date for Sunday. She would come to my place. I said we could go for a swim and do some sunbathing around the apartment pool. She said she did not do bathing suits well. It took me a while to clue in but now that I have been around the block I know wearing a swim suit is one of the toughest things a pre-op MTF transgender person can try to do.

We settled on a little sunbathing and a lot of chatting. Miniskirts were the rage of the era and Linda wore them very well. I started to recognize how she cleverly wore the towel to pad out her hips. (Years later I would often use Holiday Inn hand towels for the same purpose. Then I got The Breast Form Store’s padded panty and waist cincher, the best of both worlds.)

We talked about Linda’s rather sad childhood, about the bullying she faced for her size while she was constantly reminded by well-meaning aunts and other relatives what a cute girl she would have been. We talked again about her desire to go to Japan for sex change surgery. I expressed my envy that she was set on a goal. I did not tell her my real envy was how pretty she was and would be as a full woman. I was sure I could never achieve that level.

Then came another ‘road not taken’ moment. One road had me revealing my true desire to be one of the girls at the St. Charles even if just for a short time and on weekends. The other road would have us continue to be male/female lovers until our relationship eventually petered out. I was not destined to be in Toronto forever and at that time after the summer course ended I expected to reunite with my family.

Girls just hanging out.

I chose the path towards joining the girls. Linda helped me make the choice. She asked how I had felt when the girls made me over. “I’ve got a confession,” I told her, “I loved it. I like to wear lingerie and this was way much better.”

Just talking about it made me hard and Linda noticed. “I could tell you were enjoying it,” she said as she patted my penis. I was a bit self-conscious thinking that someone could be watching as we sat on the apartment’s sun deck. It didn’t bother her.

“Would it be okay if we did it again,” I asked, “just the two of us?”

“Sure,” she replied. “When would you like to start?”

“Right now?” My voice was cracking with anticipation.

We left the pool area and headed back to my apartment. I held her hand in one of mine while my other hand held a towel in front of my waist.

“First things first,” Linda said as soon as we were in the apartment, “We are going to have to find a way to hide that thing.”

Grabbing me by the penis she led me to the bedroom and pulled me in an embrace on top of her. We kissed deep and lovingly but she never let go of my ‘mister.’ No need to go in to a lot of details. We made love. I climaxed and ‘mister’ shrunk to a manageable size.

Immediately I had some second thoughts about the path we were going to take but Linda made it clear there would be no turning back. “Now that is done you need to shave.”

“But I shaved this morning.” I protested. She softly ran her had upwards across on cheek. I could feel the bristling.

“I bet you used an electric razor,” Linda smirked. She led me to the bathroom where she ran the hot water until she could soak a facecloth with the hottest water I could stand. “Here, soak your face and neck for about a minute,” she instructed.

I could virtually feel the skin pores opening. From her bag Linda produced one of those new twin blade razors.

“But I don’t have shaving cream,” I protested.

“Soap does the same job and is a lot cheaper,” said Linda. She showed me how to gently work the razor upwards across my cheeks and neck against the grain. When I finished I moved my hand up across my face. ‘How smooth,’ I thought, ‘Wow!’

The lesson in shaving was followed by a quick manicure job, a bit of eyebrow plucking and Linda said, “We have to do something about that leg and body hair. But not today.’

I hadn’t even thought about my body and leg hair but of course it would have to go if I were to go out. That was another ‘road not taken moment’. If I agreed to the removal of my body hair I could go out in some very sexy outfits. However the lost hair would surely be noticed back home. How could I explain it?

“Okay, let’s see what we can do about your make-up,” Linda moved on. She sat me at my wife’s make-up table with my back to the mirror.

“How can I learn if I don’t see what you are doing?” I remember asking.

“Time enough for that later. Now I want you to see what you can achieve with practice.” In little time and using her foundation and my wife’s eye liner, eye shadow, mascara and lipstick Linda had me ready to face the mirror.

Sitting there naked and wigless I actually thought the make-up made me look silly. Linda noticed my pained expression, reached in her bag and pulled out a smaller bag. “Here, we’ll try this,” she said as she opened and shook out a long blonde curly wig. What a difference the wig made! The rest of the outfit was icing on the cake. We managed to find a mini skirt, a sweater and necklace among my wife’s things as well as the all-important stockings and garter belt. That Sunday afternoon stretched in to the next few days with Linda never letting up on her instruction.

“Achieving a feminine image is far more than putting on a dress and some make-up,” said Linda. In short order she showed me how to stand, walk and sit like a woman does. To this day when I see a group of t-girls sitting at a table with shoulders hunched I think of Linda’s instruction. When I hear those same t-girls mumbling as they speak I think of how Linda instructed me in the differing musicality in the male and female voices. She told me that if I were to go in public as this new woman I would be entering a dangerous world. This was the late 1960s so she was not kidding. She told me to always be aware of dressing to fit in. I may like wearing hot pink mini-shirts and high heels and that might be fun to wear to the St Charles but it would be inviting trouble to dress like that on Yonge Street during the day. She told me advice I remember to this day, “You can avoid a lot of trouble by dressing to fit in, not dressing to offend,” she said.

Then Linda led me to the most important intersection in my life. Figuratively speaking, it was not just an old country road but we were coming to the junction of two Interstate highways and whichever road I took would send me ‘speeding’ down that highway. “How would you like to get dolled up to come to the St. Charles next weekend? I know someone who would like to meet you?”

Her look of scorn silenced my protests that I could not possibly do that. I agreed to think about it.

Almost every day over the next few weeks I faced a decision that would become a ‘road not taken’ moment. I became almost totally immersed in the Toronto drag culture of the late 1960s. It was a month that did not drag by, excuse the pun.

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Category: Transgender Body & Soul, Transgender Fun & Entertainment

Linda Jensen

About the Author ()

Canadian writer Linda Jensen is a long time contributor to TGForum. Before the days of the Internet Linda started her writing with the Transvestian newspaper. Her writing ranges from factual accounts of her adventures to fiction although frankly sometimes her real life adventures are stranger than the fiction. Linda is married to a loving partner who upon learning about Linda said, "she was part of you before I met you. Although I didn't know it she was part of the package I fell in love with. I don't want to mess up that package." "Does it get any better than that?" asks Linda.

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