On to Toronto!

By Cissy


CissyHaving flown from Finland across Scandinavia and most of Europe I finally made it to the second stop on my world tour, Toronto. Though I had a big presentation and some other consulting work to do, I was looking forward to having 3 nights free in what my research had indicated was a very TG friendly city.

I arrived into town at 8 pm, (about 4 am Helsinki time), a lot less rested than most people would prefer to be. Surprisingly, my luggage had arrived with me, an unusual feat for the airline I'd been using.

Moving my luggage through the various ports of call had been an endless source travel anxiety. I had three very overstuffed suitcases and two equally crammed carry on bags. I figured that any self respecting customs officer would be suspicious of so a called "international consultant" attempting to transport all of that stuff across international boundaries.

For all I knew the Canadians had special wardrobe smelling dogs trained to detect the presence of inappropriately placed clothing. "Excuse me sir, our dogs have detected the presence of open-toed pumps in your luggage, please come with me..."

"I don't know what you mean", I say as two Royal Canadian Mounties hustle me and my bags into a secure inspection room.

"Are you saying that you don't recognize these uh...small bikini panties...eggshell white from...uh...Victoria's Secret?"

"Oh, yeah those...they're a gift for my wife..."

"Hmm...I hope you plan to wash them before you give them to her....and what about these?...um...they appear to be homemade breast forms made of plastic bags... and (he punches his finger into the bag and then tastes it)... liquid freezer gel...looks like about a C cup I'd say."

"Oh, those...they're not breast forms...I use them to keep my uh...insulin...yeah that's it...to keep my insulin cold...."

"Right. Sir, I think we have an international wardrobe violation here, don't you? (he holds my leatherette skirt and leopard scarf)...Take him to interrogation Jennings! "

That I was actually able to avoid an ugly customs episode was a tribute to my clever portrayal as a tired and overwrought international business "man" who travels with too much luggage. Not necessarily a challenge to my acting ability. By the way, how transparent is latex. I sure hope the x-ray machines didn't pick up my happy little traveling sex toy collection.

Before going to the hotel I set out on my TG reconnaissance mission. I had prepared for this moment and was ready. I piloted my stealthy Chevy Lumina along the appointed route I had memorized during the monotonous trip. My objective, to find some of the key Toronto TG friendly clubs and businesses (mainly in an area known as "Boystown"). Following up on the information I had culled from the Internet would give me confidence about where I was going, allowing me to plan a big time for myself.

Of particular interest was The Wildside Club. An organization, housed in a residential two-flat, which offers a variety of services to the TG community including shopping, makeovers, socials, and overnight stays.

By the time I got there it was closed for the night. This was disappointing because I really wanted to hook up with one or two "sisters" who might "show me the ropes" in Toronto. I'm much more confident about going out enfemme if I have a companion or at least some first hand knowledge about the local surroundings. Tiredness mixed with disappointment and I put off finding the other Boystown clubs. I considered the mission only a partial success.

I got to the hotel and let a helpful bellman unload all 2 tons of luggage while another went off to park my car. This, I realized the next day, was a serious glitch. It turns out that they park all of the hotel guest cars in a privately run garage space several blocks away. This meant that only a bellman was allowed to get your car (a process which required a minimum of 10 minutes waiting time not to mention a tip). This access problem was especially troublesome for me because all of the TG locations I wanted to visit were several miles away and up until this point I had planned to use the car to get there.

With no companion, or good information about where I was going, I had planned to rely on the mobility and anonymity of car travel as my last source of security while “out” in public. However, this crazy retrieval system meant that I would have to spend way too much time standing, enfemme, in a busy, well lit hotel lobby waiting for a car belonging to some guy in room 2202. This posed a greater passability challenge than I cared to deal with.

I tried to see if there was a way around it. I figured that If I could get access to the car while enfemme, I would still have my “crutch”. All I needed was the keys and the car’s location and I could travel freely, risking only minimal exposure during brisk walks to and from the garage.

I asked the parking concierge if I could get my own car. "Why would you want to do that?", she asked.

Uh-oh...she already seemed resistant. If I could just get the keys and the location then I'd be back in business. "Well, actually I just need to get in there...I uh... left something I need in the trunk."

"Oh, well a bellman can get the car for you..."

"Can't I just go over there and get inside?", my hysteria level started to pick up

"No! The bellman has to do it!", various and sundry insults flooded my thoughts.

That's it, I knew it! They were keeping my car hostage! They were intentionally trying to confound my efforts here. I needed a devious plan.

Off to the drawing board...

    1) I could call room service and order a seafood salad (seemed like a good enough choice)...

    2) when the bellman got to my room with the seafood salad, I would invite him in, have him put it down on the table...

    3) then I'd take him by surprise, pull a pair of tights (I had a pair that got a run in them in Helsinki) over his head, tie his hands with the stocking legs, force him to the ground and make him tell me the secret location of my car.

Or I could just give up... I was running out of energy. Solving the endless array of elaborate “going out” problems that challenged me throughout the trip had worn me down. Had I been more energetic I might not have submitted to circumstances. But now I bowed to the forces of the big city. I realized that I would have to take cabs which limited my mobility and increased my sense of exposure.

The next day I tried to reach somebody at Wildside. I sent e-mails, left phone messages...no response. When I finally got somebody, they told me that they really couldn't help and that I should call back later and talk to "Jennifer".

Looking back on it, I should have just put some "dress up clothes" in a bag and gone over there. For $10.00 CND you can change there and be right in the middle of TG Grand Central Station. But for some reason I had convinced myself that I had to make the "transition" in my hotel and then go over there. I was trying too hard, getting too obsessed and now I was mentally disabling myself by misperceiving the situation.

When my conference was over for the day, the thought of dressing up and making what seemed like another ocean crossing into Boystown was overwhelming. I had stopped having fun.

I called Wildside and finally reached Jennifer the TG store "manager". She recognized me (probably as the overanxious out of town cross-dresser) from my various attempts to contact her. In addition to inviting me to the store for a visit, she encouraged me to go out and have fun. She told me that Toronto was okay, that cabs were okay, and that anyplace I visited in Boystown promised to be a good time. I wasn’t satisfied with this. I wanted her to send the TG rescue squad.

“10-4...we got us another cross-dresser in distress at the Hilton. Send the usual personnel... a therapist, a wardrobe specialist and Mary Kay Distributor...10-4..over...”

It was time to give the whole thing a break. I decided to take the night “off”.

I had dinner with some people from the conference and got back to my room early. I regarded my luggage longingly and ran my fingers through the lingerie in my “girl” drawer. But I just needed a night off. I slammed the drawer shut, resolving to neither dress up nor go out even though I had very little time left in Toronto.

The next morning (my last full day in town), I awoke with renewed energy. I was scheduled for an early dinner session and decided that as soon as it was over I would get dressed up and do the town.

The day before, I had discovered that many of the major downtown buildings, including the hotel I was staying in, are connected by a series of tunnels which double as a sprawling (about 3 miles worth) shopping mall. In addition to having run a particular credit card up to its’ limit on a remarkable underground clothing sale, I realized that these winding catacombs provided an excellent after hours escape route from the hotel. Now I could avoid the lobby all together, take the elevator to the tunnel level, wander past some closed shops, and surface through a street access exit several blocks away.

I made it through the day driven forward by my renewed TG spirit. Also, my time was running out because I would soon return home where my freedom to dress up would be very limited.

My client was a little late but dinner was underway by 6pm. We were well into the main course by 6:30 and I optimistically calculated that I would be back in my room getting ready by 7:30. The client was curious as to why I was eating so lightly, after all he was sponsoring a gourmet dinner and I didn’t seem to be taking advantage of the situation.

“Well, Jack, I’ll tell you. I’d love to pig out on all of this great food but you see right after dinner I’ll be cramming myself into a size 28 waist cinch and a size 9 black mini skirt and if I have so much as a glass of water, I’ll look like a woman in a sausage casing. Know what I’m sayin?”

“Sure guy. Goes without saying, think nothing of it”, says Jack

Yeah right...

Actually I feigned the remnants of a nasty Scandinavian flu virus that had been hanging on and added a shallow little cough for effect.

Jack was taking his time, a second drink, then a third, and we hadn’t even talked business yet. He was obviously making a night of it. A nice break from the wife and kids. The evening was stretching out, 7:45 and we still had some key decisions to discuss. And now he was ordering coffee. By 8:15 the decisions were made, the coffee was gone, I could be ready in two hours and to one of the bars by 11:00 (most were open to 2am).

That’s when Jack decided we should have a drink. “We’ll go back to your hotel, I know a great bar there...”

So near, yet so far away. I was sitting in the lobby of my own hotel, drinking unwanted quantities of sparkling water (ever try and use the ladies room while wearing a full length body shaper...not an easy task)dying to escape to my room. I had been anticipating my conversion all day, the pressure was growing,

I was becoming a hormonal reactor. At any moment I would have one of those sudden and terrifying sci-fi like changes. My clothes would tear, my face would morph, and when the dreadful screaming was over I would emerge as the Incredible Slut, hot pink vinyl mini skirt, flame red hair, smoldering stare and 4 inch heels.

At 9:00 pm I was finally able to make a suitable excuse. Free at last.

By the time I got back to my room, I could feel the fatigue setting in again. I needed a serious shave, I wanted to do my nails, I was feeling stuffed from the endless dinner I tried not to eat, and in spite of all the encouragement from Jennifer, I didn’t feel good about taking cabs to unexplored places. I sat down on the bed and started to think the whole thing over.

The elements of the dilemma danced in my head...a kaleidoscope of pleasure and anxiety. I really needed to be the feminine me but I didn’t want to deal with the complications of going out. A year ago this wouldn’t have even been a problem. Back then I was happy being closeted up in my hotel room, fearful of any exposure to the real world. But now, and after some great success at going out the choice to abstain felt like a serious defeat.

I concluded that I would hold off on the going out decision. I would get dressed up and then if I felt like it I would head to Boystown.

I felt the old energy returning. Side stepping my self generated complications helped me shed the depressive cocoon that was forming. Now I felt like I wanted to do something special. In addition to the usual shaving and make-up routine, I decided to go for the dark red nail polish.

I was determined to do it right this time. Filing, buffing, clear coat and then the red. I was patient, applying one coat at a time. I sat there at the edge of the bed, looking very sexy if I say so myself, all made up, wig in place, a blue satin nightshirt over black lace. I waited as the last coat dried, fingers spread, hands useless. A warm flush of sexiness washed over me. I allowed myself to feel the submissiveness of this self imposed bondage. This sort of helplessness, not normally in harmony with my aggressive male nature, provided both an odd sense of relaxation and a kinky sexual thrill.

It was getting late, if I was to going to get to any outside location I needed to start moving. The Television had been blaring in the background and as my reverie dissolved I noticed that a post news sports show had come on. This, I decided too much testosterone for the mood I was trying to maintain so I reached over to switch to something more gentle. That’s when the bottle of red nail polish fell.

During my little submission fantasy, in addition to the mental impairment which comes from inhaling toxic enamel fumes, I had failed to tighten the bottle cap. Now I looked on in abject horror as the bottle fell, moving in the same slow motion that all horrible accidents seem to occur in. I watched it twist through the air, throwing liquid like a Spin Art machine. Its’ rotation created a shiny thick red spiral which floated in air and then soaked into thirsty carpet below. When the bottle hit the floor it continued to spin, putting a final flourish on the large cursive letter “O” which was produced during this artistic fiasco.

It seemed that everything I did to minimize the damage only made things worse. What had been a slim cursive “O” was now a thick cursive “O” and two brilliant white hotel washcloths were now permanently dark red. I used all of the nail polish remover I could (I needed to save some for myself or I’d be wearing gloves in public until I could buy some more) but there wasn’t enough. It was 11:30pm and the local stores were closed. I had no easy means of getting to an all night convenient store and I wasn’t about to call housekeeping.

“Hello, housekeeping this is the guy...uh (whoops change voice) ...lady in room 2202. I seem to have spilled some nail polish and..uh, who?...Mr. Boden?....no there must be some kind of mistake this is Ms. Boden...no Mr. Boden here...I seem to have...what? No the credit card information must be wrong this is Ms...what? what gender police? Mounties...coming now...but ...”click”...”

Having done what I could to control the stain, I once again gave up. In the morning I would get the necessary materials and try and clean the stain. If I couldn’t make any significant progress, then I would turn myself into hotel authorities. Meanwhile the “O” would have to lie there, the result of cosmetic foul play, a nail polish corpse.

11:45 pm. I picked out an outfit, feeling a twinge of guilt and stupidity each time I passed the big red “O”. No matter what I wore, partly the result of limited shopping opportunities, I looked pleasantly slutty. I accepted the obvious limitations of my wardrobe and dressed for sexcess.

Determined now to go out, I pulled on my leather jacket (a nice “uni-sex” item)passing the full length mirror on the way to the door. What an image I created. I stopped to admire myself, short black leatherette skirt, slinky leopard pattern blouse (the “cheap” freezer gel breast forms worked great), high heels, lots of dangling jewelry, motorcycle jacket and tiger stripped scarf. With my long red curls and evening make-up I looked just like a...what’s the word...Hooker. Yes that’s the fitting description here.

So let me see if I got this right. I was about to wander the empty downtown streets of Toronto looking for a taxi, at midnight, on a weekday, in high heels, looking like a working girl. “Yes, that’s right”, I answered to myself. Okay, just checking.

The halls were empty. The wall sized mirror near the elevator reflected my image in the as it appeared in the greater context of the hallway. Little, sexy, very passable, not quite as sluttish as I appeared close up in my room. I looked hot but not necessarily, “on the job”.

The elevator opened up on the Lobby because I had pushed the wrong button when I got in so I pushed the Ground Floor (tunnel level) button and waited for the door to close. It didn’t. I coaxed it again but no response. As this was going on a guy, young, well dressed, good looking and really drunk walked past the elevator. I thought I recognized him from my visit to the hotel bar hours earlier but I couldn’t be sure.

He spotted me, who wouldn’t. I suddenly felt like I had a neon sign that said “hot and easy”. He stopped, faced me and started to say something like “Hey, baby. Where are you going?”. I waved politely with my left hand and urgently jammed the pretty dark red nails of my right hand into the Ground Floor button.

With all of the sex fantasies I had entertained on this trip, many of which involved a romantic tryst with a guy like this, I was just plain scared. This was not how this was supposed to unravel. He stumbled toward the open elevator, smiling sloppily and mumbling something about being new in town when the elevator door finally closed. The car shot down to the tunnel system.

Hopefully, Mr. Right didn’t have the wherewithal to follow. When the door opened I jumped out of the elevator and moved as quickly as my little heeled feet would take me. I headed for a nearby ladies room and found that it was locked. No escape hatch available.

I steadied myself. There was nobody following. Nothing bad had happened, I just met a drunk guy that’s all. The area was probably under surveillance by a million cameras and a hotel security guard was probably within shouting distance. The only thing out of place down here was me. The borderline hooker, wandering around an empty hotel at midnight.

I headed for the tunnel system, figured I would surface about a block away and hail a cab (that’s if there were any cabs...I had a feeling that the action at street level might be pretty dead by this hour). The tunnel floor was covered with glossy ceramic tiles, making foot travel difficult for a high heel novice like myself. I moved precariously, reaching the doors which separate the hotel from the rest of the system. Naturally, the doors were locked. Had I been paying attention earlier, I would have noticed the signs (fairly large at that) which announced that the system closes between 12 and 5am.

Oh yes, the proverbial “last straw”. I suddenly decided that this adventure was over.

It was late, a weekday, I was dressed like a hooker, drunks wanted me, I had a “corpse” in my room and now the exit was closed. On top of that, I had no idea of what other challenges waited for me on the empty streets above. I headed back to my room.

The “O” was still there. I threw a towel over it and changed into my favorite lingerie. I stayed enfemme that night, comforting myself with quiet music and sensuous play (might as well use those toys I’d been dragging through international airport security posts), and slept peacefully until it was time to get up and buy more nail polish remover.

I was glad that I had given myself permission to “not” overstep my limits the night before. This had been in itself a very positive, nurturing and feminine response to a personal challenge. Unlike my typical masculine response, which would be to take unnecessary risks in order to win, I was beginning to learn something important from my previously untapped “feminine” side.

Although I was sad that I had missed out on some opportunities to be “me” on the streets and in the TG safe places of Toronto, I knew I would be returning and would have a chance to try it again. I was leaving there a little sadder but wiser. The new nail polish remover had worked well enough on the stain to diminish my guilt, leaving only a faint reminder of a stupid if not hazardous cosmetic spill. And as my luggage and I waited for the car, I smiled, sharing a little joke with myself about how I had indeed left my mark on this town.


Back to Transgender Forum's home page