Crystal's StorySite

A Trip to Toronto                    by: Debbie Cybill


It all began when I told my wife Chantal that I had to go to Toronto for a meeting at the university. This was a regular meeting that I anticipated with pleasure, for I should meet with old friends and colleagues from other universities.

"You can’t fly until you are fully recovered," she said, "Why don’t you go by train?"

I was recuperating from a spell in hospital and this trip would mark a major step in my recovery, my first trip away from home.

"Right, train it is then," I agreed.

By air Toronto is about 75 minutes, but if you add the time in the airports at each end it is almost 3 hours. By train it is three hours with no messing about in the terminal, and much more comfortable. It seemed like a good idea to me. I certainly was not intending driving the five hours at this time of year.

"What shall I wear?"

For the meeting itself I should need a business suit, but sitting in that in a train would result in wrinkles, so I was asking for suggestions for my traveling garb, sweats, perhaps, or slacks and tweed jacket?

"Why don’t you wear your teal green suit?"

I looked at my wife open-mouthed. My teal green suit consists of a sleeveless tweed dress with a matching jacket over it. I often dress at home and sometimes even go shopping with my wife en femme. I have even, on a few times, been to the theater with her, usually in a matching dress. She loves such occasions when we look like sisters. But to go to Toronto alone en femme, without her, that was too much. And it was a business meeting.

"You can do it, Debbie." She called my by my femme name.

I shook my head and looked at my toes.

"I dare you!"

That did it. She knew I would never refuse a dare. Could I really get away with it? I could at least try. My VISA card just has my initials on it - Dr DB Cybill - so there should be no trouble there. But what to pack? I pulled my garment bag out of the closet and set a few clothes on the bed. My masculine three-piece suit that I should wear for the meeting, a little black dress for evenings, underwear - all femme, of course - masculine dress shoes, a pair of black patent pumps with four inch heels, a dress shirt and tie. That should do.

The next morning, Thursday, I showered and shaved carefully, not just my face, but my whole body. No-one would see my body, but a shaved body makes me feel so much more feminine. I pulled on my mint green satin panties, tucking myself away with care. It was a cold morning so I pulled up a pair of robust, shiny, black tights. My bra matched my panties and supported my heavy breast forms. This was going to be a day for layering against the weather so I added a camisole and then a full slip, dainty with lace. I sat at Chantal’s vanity and started on my face. My beard is slight and blonde, so it took little Clinique foundation to cover it up. A touch of pale tan Clinique powder to set the foundation and I was ready to start painting this blank canvas. A little darker tan blush to heighten my cheekbones. I outlined my eyes in dark brown eye liner, with an even darker shade of brown mascara. I painted my upper lids with earth tones; I looked in the mirror and liked what I saw, good makeup for an office worker in the day time. Chantal looked over my shoulder and nodded her approval.

"What color lipstick are you intending using, darling?"

"I thought Elizabeth Arden bronze. What do you think?"

"No. It’s too metallic for daytime. I suggest you stick with Clinique. Their bronze is more suitable for day."

I outlined my lips with a pencil and then filled in with Clinique bronze.

"That looks good, Debbie. What jewelry are you intending wearing?"

"I thought perhaps a single strand of pearls and pearl earrings."

"Not both pearls and earrings in daytime, dear. That is for evening. Stick to just the necklace. And what rings will you wear?"

Chantal was keeping me on a short rein, I thought, and teaching me to be more feminine at the same time. If she thought I did not know how to dress and behave as a woman why was she sending me on the train like this?

"I shall wear my wedding band, of course, and perhaps that diamond cluster to gave me last year."

"Which hand will you wear that on, Debbie."

"My right hand, I think."

"It’s really a cocktail ring, sweetheart, but it will do for daytime if you wear it on your left hand alongside your wedding ring." The implication that it would look like an engagement ring was not lost on me.

While this discussion was in progress I varnished my nails, three coats of bronze Clinique to match my lipstick and one of gloss. I put on my short wig, a little more golden blonde than my own fair hair. Chantal brushed it out for me, back combing it into an upswept style. I slipped into my boots, knee-high black calf with narrow 3 inch heels.

"I hope it doesn’t snow while I’m in Toronto. These would be ruined," I hoped out loud.

"I think you had better wear a scarf in this weather, Debbie. Here’s one of mine."

She handed me a green silk scarf with a pattern of horse harness on it. I recognized it as one I had bought her at Hermes in Paris last year. I knotted it around my throat, hiding the pearls and reached for my coat.

"You can’t wear that one, Debbie. It does not look feminine enough."

It was my goose-down parka, olive drab in color and just the thing for this weather I thought. Unisex enough to wear both en femme and en drab. But not feminine enough for Chantal, it seemed. She reached into her own closet and brought out a chartreuse, quilted, goose-down coat, knee length and zippered down the front. Much more feminine looking with its nylon texture. It would be a wee bit short on me; Chantal is a tall woman at 5' 10", but still 2 inches shorter than me. She spritzed me with pefume, Nina Ricci’s Airs du Temps.

" What are my colleagues going to think when they see me in this coat tomorrow?"

Chantal drove me to the station in her red Miata.

"Bye, darling," she waved. I wished she were coming with me, but I knew she needed to go to her office. She was going to be late as it was. It was unlikely that anyone at the Museum of Civilization would worry about their curator of Indian artefacts turning up a couple of hours late.

Now I was on my own. I could not back out. I threw my briefcase into the basket of my walker and draped the garment bag over it. This walker was a damn nuisance. I hoped I would soon recover enough to walk without it again, but on this occasion it proved useful. I did not need to carry my baggage. It proved useful yet again when I joined the lineup for the train. An attendant pulled me out, escorted me through the barrier and helped me onto the train.

It was a comfortable trip, much more comfortable than a crowded sardine plane, even business class, and I was able to reread all the documents for the morrow’s meeting. I looked around. Not another skirt in sight. In Canada skirts disappear at this time of year only to reappear in the spring. Only office workers wear skirts in winter, and there were none of them on the train, at least none in office wear.

In Toronto an attendant helped me down and led me to the taxi rank where again I jumped the queue. That walker did draw attention. At the Meridien Hotel on Bloor street, the fashionable quarter of Toronto, I checked in as Dr. DB Cybill and the clerk welcomed me cordially, evidently taking me for a woman. I had worried that my voice would give me away, but my sulky contralto femme voice worked well. The next worry was that some of my colleagues might have chosen the same hotel. The room was standard drab with two king sized beds, two upright chairs, two easy chairs and a small table. At least there was a jack for a computer. I threw off my coat and scarf and hung up my jacket and my garment bag before plugging in my laptop to email Chantal that I had arrived safely. I kicked off my boots and put on my fluffy mules instead and then surfed the web for a few minutes. I found a few new stories on Crystal’s Storysite, and one of those would provide bedtime reading.

It was time for dinner. I hung up my dress and opened my garment bag. I kept on the same underwear but slid off the tights. For evening I was going to wear sheer stockings and a garter betlt. I wondered if my bulge would be controlled just by my panties. Not to worry. If a bulge showed and anyone commented I would just brazen it out. I ran a hand down my slip and looked in the mirror. No bulge. I pulled my LBD out and held it up against myself. In the mirror my slip was clearly too long. I took it off. The LBD was gauzy, much of it constructed of organdy with satin accents. This underwear would not do; it would show through the dress. I stripped off, put my wig on its stand and took a quick shower after removing my makeup. I should need heavier evening makeup. I dusted myself with talc and pulled on my black bikini, small enough to hold me in well, a mere wisp of lace but with hidden strength.

I slipped my arms into a black matching bra. After all my years of practice I could manage to fasten it behind with no trouble. None of this fastening it in front and twisting it around. My breast forms, then my black camisole. I fastened a black lace garter belt around my waist, tucked the garters inside my panties, and sat at the vanity to make up my face. The same foundation, but a little more blush, the eyes darker and with some green in the palette of colors that I used on my upper lid. I tried the metallic bronze Elizabeth Arden lipstick, liked what I saw and reached for my longer blonde wig, the one I only wore in the evening, never in the day. You see how well Chantal has trained me! I put the drop pearl earrings through my ear lobes and replaced my pearl necklace. I looked in the mirror and saw that I showed some cleavage. I rubbed a little brown blush there to emphasize it.

My stockings, sheer black nylons with a seam, I rolled up my shaven legs and clipped them onto my garters. Slipping my feet into my black patent pumps I stood up and thought I looked good in the mirror. Now was the moment. I help open my black dress, stepped in, settled it around my shoulders and admired myself in the looking glass. This was a new dress that Chantal had bought me after I came home from hospital, not form-fitting but loose. Since my illness I could no longer wear my corset so I was rather thick in the waist. My old fitted dresses would no longer fit me and I needed looser dresses like this one, that came down to about 3 inches above my knee. Rather short for a woman my age I thought, but evidently Chantal thought differently and I trusted her taste.

I looked at my nails, too short for evening I thought. It had not really mattered on the trip when I wore green leather gloves, but for dinner I would prefer something more feminine. I cleaned off the varnish and took a new packet of stick-on nails, not too long since a woman of my age would not wear really long nails. I stuck them on with two-sided tape. That would last the evening, I hoped. I used Elizabeth Arden’s bronze varnish to match my more metallic lipstick. A touch of perfume between my breasts, behind my knees, inside my elbows and behind my ears and I was ready. Not Air du Temps this time but something a little more musky and fit for evening, Christian Dior’s Obsession.

I telephoned the main dining room, up on the roof top and booked a table for one and picked up my evening clutch. I make an impressive woman with my height increased by my heels and I towered over the maitr d’.The restaurant was half empty when I walked in but the maitre d’ seated me at a table near the door to the kitchen, as so many of them to single women. I was having none of that and made a fuss, resulting in a fresh table in more pleasant spot, though one that was rather visible to the other diners. I didn’t like that, since I was not trying to catch attention, but I did not want to make a fuss again.

The meal was better than I expected, good hotel food, but not up to the standard of a good independent restaurant. Lobster bisque to start with, too salty and not redolent of chunks of lobster; a salmon steak to follow with sorrel sauce. The sauce was good but the fish was overcooked. I should know better than to order fish in anything but a seafood house. I drank a bottle of undistinguished chardonnay, an Ontario wine from Hillebrand Estates. I looked around, wondering if any of my colleagues was eating here. I saw no-one and breathed a sigh of relief. I decided to have a cognac in the bar and moved there.

I soon noticed a man looking at me. I was sitting in a booth and I just smiled back when he smiled at me. Then, to my horror he started walking towards me and I realized that it was my colleague William Loomis from Windsor university who was the youngest member of our committee, at least 20 years younger than me. Had he recognized me?

"I noticed you sitting all by yourself at dinner. And now here you are alone again. I’m Willie. Can I buy you a drink."

So he called himself Willie, did he, when he was on the prowl. I picked up my snifter which had very little left in it.

"Your glass is empty. Cognac is it."

There was no help for it. It was so long since any man had hit on me that I had forgotten how to cope. At least he did not seem to recognize me. Before I could decline he had called the waiter over.

"I would love another cognac," I said.

That was a mistake, I realized at once. Now he would sit down and talk to me at close range.

"I’m Debbie." I held out my hand expecting him to shake it.

"Enchanted, Debbie." He took my hand a kissed it. With my nails my hand looked quite feminine but the back shows my age better than any other part of my body.

Now the husky contralto voice that I had cultivated for so long turned out to be a trap. It sounded sultry and sexy. In my own ears I sounded as though I was coming on to Willie. The waiter appeared with our drinks, cognac for me, bourbon for Willie. I felt his hand on my thigh and tried to brush it away. We chatted for a while as I tried to defend my thighs from his advances.

"Shall we dance?"

The trio that was providing the music seemed to have a repertoire of slow oldies, so dancing would be cheek to cheek. Still, I enjoy dancing and move well in heels, even dancing backwards. Besides I could not see how to refuse him. He toak my hand and we moved out onto the tiny dance floor where we were the only dancers. His right hand crept down towards my butt and he clutched me more tightly. I could feel his hardon rising as he pressed it against my belly. It felt good to be able to turn on a man this way. It made me feel more confident in my femininity. The song ended and Willie escorted me back to the table. He stood with his hand on the back of my chair and I thought he was about to pull it out for me. Instead, he grabbed me and kissed me, trying to force his tongue between my lips. I smacked his cheek.

"Why don’t you go and find someone your own age, Willie."

I spread my left hand to show my rings, the diamond cluster next to my wedding ring. "I’m not that kind of woman. Goodnight."

I stalked out. Fortunately, Willie did not follow me. I certainly did not want him to find out the number of my room. Back there I stripped off, hanging up my clothes and wig in the closet, creamed off my makeup and pulled on a nightdress. I watched the late night television for a few minutes to settle my mind and then fell asleep.

The next morning I rose early, shaved and examined my face in the mirror to ensure that every trace of makeup was gone. I peeled off the nails and cleaned my own nails with solvent to remove the slight traces that remained there. I s howered and washed my short hair, then I dressed in my peach panties, bra and camisole and pulled on a pair of black pantihose before putting on my shirt and tying my tie. With three piece suit I looked the epitome of a businessman.

At breakfast I ran into Dr William Loomis. I had butterflies for a moment thinking about last night.

"Hello, are you staying here, Liam? I didn’t see you last night." The hell I didn’t. I may not have seen Liam but I had certainly seen Willie.

"Yes, DB. Did you dine out last night? I dined upstairs. Let’s share a taxi to the university."

"Better make sure it has a good trunk. I have to walk with this thing for the time being." I indicated my walker. Thank god I had not taken it in to dinner last night or he would have been sure to have recognized me.

"I’d heard you had been sick. Are you recovered now?"

"Very nearly, but I need this thing to make sure I don’t fall over."

We ate our breakfasts, chatting as we did, then returned to our rooms to collect our briefcases. I discovered with some relief that he was not on my floor. I slipped on my chartreuse coat, or rather Chantal’s coat.

"Did you borrow that from your wife, DB?"

"Is it that noticeable? When I pulled my goose sown parka out of the basement closet it was full of moth holes," I extemporized. "My wife insisted I used hers, swearing that it would not look too feminine."

It was a good meeting and it was great to meet so many old friends and colleagues. Most of us dined together that night at Le Bistro du Cite, where the food and company were both delightful. Dear Willie was absent from our gathering however. I guess he was busy prowling after women.

I next saw him while checking out from the hotel. I was en femme again, in my teal green suit and daytime makeup. He recognized me from the night before and tried to take up where he had left off. Fortunately I had left my coat, Chantal’s coat, with my walker in my room, intending to put it on just before leaving. That would have been a real give-away.

"Shall we share a taxi to the airport?"

"I came by train, Willie."

Altogether close run!

The trip back in the train was uneventful, a delightful ride along the north shore of Lake Ontario, just rimmed with ice now and looking quite beautiful through the trees. One other skirt this time, a student in gothic makeup and clad entirely in black velvet.

I was grateful when Chantal met me at the station and I had to tell her all about it. She had met Liam Loomis and was delighted about my adventure with him.

I always thought he was a Lothario, but never thought he would try to hit on you, Debbie, or even on me; I’m too old for him."

"Willie?" Indeed!


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