Montreal Marathon — And a Bit More…

When they come to write my obituary I think they will be able to say, “She (he) was passionate about life.”

In my younger days I loved playing sports – hockey, soccer, skiing, softball and football – I played them all.

However at one point in my life I re-discovered transgender tendencies that had lain dormant since my early teen years. Then followed my desire to cross dress and transform my body by removing body hair and letting my hair grow. I knew that would lead to questions among my team mates so I made excuses to quit my life of sports.

That led to an unwanted consequence. When one cuts down on one’s amount of activity but does not cut down on the corresponding dietary input there often is a serious consequence and you see it in a lot of ex-athletes. I gained lot of weight, most of it in very unfeminine places like my belly and under my chin.

I soon realized that if I wanted to keep fitting in to my favorite dresses I had to reform my life.

My answer was to go on a diet and to take up a regime of fitness including a lot of running and cycling. I lost all that weight and more while gaining some ‘feminine form’ by way of a slim waist and a pretty nice butt. I also learned that in cycling circles it is considered normal for men to shave their legs. I really embraced cycling for that.

My running led me to seek out marathons and other distance races in cities where I could go to run the race and also spend several evenings out as Linda. Los Angeles, New York and Chicago benefited from my tourist dollars as Linda visited the clubs and my male alter ego ended the visit running a marathon.

My partner knew of my passion for running but did not share it. She also knew of and accepted my passion for being Linda but had no desire to share in the activity. She had no desire to come with me when I went on running trips. She knew I preferred to bring ‘Linda’ along.

That led me to the Montreal Marathon. Held in mid-September of each year the Montreal Marathon has a reputation among runners of having a very scenic course and one of the best expos and social schedules going. But that was not what attracted me to Montreal. I knew from first-hand experience that it had several ‘drag clubs’ including one of North America’s best and my favorites, Club Cleopatra.

By going to Montreal on the Thursday before the marathon I would have several nights out en femme before the race on a Sunday. I expected what had become a fairly routine race weekend. I would check in to get my runner’s kit, go to my modest hotel, which just happened to be very close to the Cleopatra club, dress as Linda and head out for the evening; repeat on Friday and Saturday. Thursday would be quiet at Cleopatra’s but the next two evenings would be busy with a lot of the local TG members dropping in, bachelorette parties and the usual crowd of ‘admirers.’ I expected to also squeeze in a shopping trip or two en femme.

Cleopatra’s

However what happened Friday evening was anything but ordinary. It turned out to be one of the most erotic experiences of my life. I was at the Cleopatra getting ready to watch the early show. I had been dancing with a few of the local ‘sisters’ but decided to take a break. I definitely was dressing to try to impress with black lingerie under a black and white mini skirt, and a low cut black blouse.

As I positioned myself, cross-legged, on a stool at the front bar Serge, the bartender put my favorite drink, a Bailey’s Irish Cream in front of me. He told me, in French, that a gentleman opposite had asked him to give me the drink when I returned from dancing. I looked over and there was a tall, very handsome and very athletic gentleman, probably in his late forties toasting his glass to me. I returned the toast and motioned for him to join me. He came over but asked if I would prefer a table in one of the quieter booths. His accent seemed British. I agreed to move to a booth. My new friend passed a few dollars to Eric, the doorman/bouncer and we were shown a table. Such tipping was not necessary in Montreal but it didn’t hurt.

My new friend, Tim, complemented me on my look and on my dancing. I replied that I enjoyed both the dressing and the dancing.

I gave Tim the ‘do you come here often?’ line.

“My first time,” he replied. “I’m in Montreal to run the marathon on Sunday? Have you heard of it?”

“Yes, of course.” I did not let on that I would also be running. “Where are you from?”

“Originally from England but now I live in Texas.”

“That is a long way to come for a race?”

“Well, I had another motive. I really wanted to meet you girls at Cleopatra’s. I’ve heard you are the prettiest anywhere.”

“That’s very flattering. So do you agree with what you’ve heard?”

“Well frankly I was a little disappointed last night. The girl I met was pretty hard edged and didn’t speak much English. It was also all I could do to keep her from smoking in my hotel room. She was definitely not my type.” Tim had wasted little time in letting me know he was looking for company.

“What type is that?” I asked with bold anticipation.

He looked straight at me and started to describe what I was wearing, my eyes, my hair colour and even my lipstick. It was a pretty good line to use on someone as vain as I am. I was also pretty impressed that he could see all that in the diminished light. It occurred to me that he must have been watching me for some time. He then went on to say that he was looking for someone who could carry a conversation, was interested in life and ‘was good in bed’.

I backed off a bit and changed the subject. Instinct told me to not seem too eager.

“So what is it you like about running?” I asked.

“Everything,” he replied. His eyes lit up as he went in to describing the beautiful feeling of a runner’s high, the up close look at new landscapes and the camaraderie of the running community, all feelings that were very familiar to me. I was able to ask knowledgeable questions and nod appreciatively at his comments. We were really hitting it off so much so that when his ‘date’ of the previous evening came over he curtly brushed her off.

I knew that if I were a regular at the club I would have been in trouble of poaching someone’s ‘meal ticket’.

The show began. For a while Tim and I watched it as I translated some of the better French lines. Soon, however, we found we preferred our own quiet conversation to the distraction of ‘Lady Brenda’ and her girls. We talked about Tim’s work with a world leading micro-electronics company, about Texas and of course about running.

Tim and I spent an hour or so together at the club before he asked if I would like to join him at his hotel. I agreed. We left by cab as Tim gave directions to one of the better hotels in town. In the cab Tim put one arm around me and pulled my shoulder over to him. He turned my face so we could kiss and he rested his other hand on my thighs. He kissed so gently I felt myself swooning. His strong hands were also very gentle. This man knew how to please a woman – any kind of woman.

We made our way to the hotel’s top floor to find Tim’s room was actually a junior suite, complete with kitchenette and Jacuzzi. Tim offered me a drink from the mini bar. I accepted. He settled for a Perrier.

“Do you mind if I slip in a movie?” Tim asked.

“No problem.” The movie turned out to be a pretty good bit of drag porn.

We had watched about five minutes of the movie, kissing as we watched when Tim suddenly said that he wanted to take a shower and would I like to join him.

“I can’t get my clothes wet,” I protested.

“Well you can take off that skirt and blouse but I’d love to see you get wet in that slip you are wearing.” He stood up from the couch and held out his hands to pull me up. He saw my reticence.

“Oh, I might as well take care of this, now.” Tim pulled three crisp Canadian $100 bills from his pocket and put them on the table partly under my purse so I could clearly see the value.

“Hey, I’m not. . .” I started to say I was not a whore but I stopped myself. I had turned down lots of offers for $20 blow jobs but perhaps I had found my price. It also dawned on me why the local girl had looked so angrily at me. She had convinced Tim that the going price for a Cleopatra girl was $300.

I let the money stay there and by so decided that I was going to take a shower, lingerie and all.

From there things got very hot, wet and steamy. I could describe the rest of the evening in great detail but I’ll refrain. Besides all of us have ‘been there; done that,’ right?

Fast forward about two hours.

I didn’t want to leave but I knew the ‘meeting in the morning’ routine was probably going to unfold.

Tim returned and it was my turn to use the bathroom. I took my purse with its makeup but left the money on the table. I freshened up my make up as best I could but frankly that was difficult as my facial hair was starting to show. I didn’t relish the thought of exposing myself to the lobby staff and to the cabbie who would take me to my hotel. The only consolation was that they had probably seen it all before.

When I returned to the living room Tim was sitting in a hotel robe. I went to put down my purse and notice two more $100 bills had joined my three.

“What are your plans now?” Tim asked.

“What would you like?”

“I would like it if you stayed the night,” he replied.

“I would love to but my makeup is already a mess and it will be worse in the morning.” I hated being practical but I’d been in that situation before.

“Well, I can lend you a razor if you have the make-up and it will give your lingerie a chance to dry.” (Did I mention that at one point we had showered together?)

That settled it. I did have makeup essentials with me and it would be nice to have dry underwear. I hung my lingerie on the back of a chair. Tim turned out the lights and we settled in under the covers. Tim spooned up against me. Given the turn of events of the evening I had a little trouble getting to sleep but drifted off shortly after hearing Tim’s soft breathing.

I’m an early riser and the next morning was no exception. I slipped out of bed, took my purse and makeup to the bathroom, showered, used the razor with a new blade and fixed my makeup. Moving to the living room I saw that my panties, slip and bra had all nicely dried. I dressed after re-applying the tape to create my cleavage.

Then I turned on the coffee machine. The aroma must have wakened my sleeping giant as no sooner was the coffee ready than he appeared, took a quick shower and re-appeared. By then I had the eggs cooking and toast in the toaster. Tim came up behind me at the stove and gave a gentle rub to my groin. He kissed my neck and said ‘good morning sweetheart.’ I got the feeling that was a routine he acted out with his wife most mornings of their life. It felt good.

We had breakfast and time asked what my plans were for the day.

“I haven’t got any,” I replied as if to say my day was his.

“Well I’m supposed to join some people for a friendship run,” said Tim referring to the tradition at many marathons where the participants have an easy jog together the day before the big race. I know because I was supposed to be there, too.

“What time it that?” I asked.

“Noon.”

“Well, that gives us some time together before you have to go.” I smiled and winked.

“You read my mind.”

We finished breakfast. Tim made sure the ‘Do Not Disturb’ sign was on the door and we brushed our teeth before adjourning to the bedroom.

Let’s just say that our sex was as good as the night before but inevitably we had to part, Tim, to his friendship run; I to bed. I asked Tim if he would be returning to Cleo’s that night but he said he wouldn’t. This run was to be his best chance to ‘qualify for Boston’ so he needed a good night’s sleep.

I understood. My goals for the race were not as lofty but after two great sex sessions with Tim I was ready for a relaxing evening anyway.

We parted. I would like to say I saw him in the race but I didn’t. If he saw me I’m pretty sure he wouldn’t recognize me. I was now the balding runner with the very contented smile on his face.

However, I did see from the online results that Tim finished about an hour before I did and thus made the qualifying time for the Boston Marathon. The next April, I looked in vain for his name in their results. Perhaps the girls at Jacques proved too much for him.

Tags: CD erotica, crossdressing, featured

Category: Transgender Fun & Entertainment