Entry #12: Shopping

Annie loved to shop. It didn’t matter what city we were in, she always brought back her latest purchases to the hotel to show off. I don’t know how she found the time with her regular day job and the fact that we always had plans of some sort for the evening. She was obsessed with always having the latest fashion and she would do her research to find the appropriate event or in-place for us to go so she could dress to kill.

I am not much in the shopping world, but have to admit that her constant desire to be in dress up mode did start to affect how I dressed as well. I couldn’t let her be seen with a bum when going out on the town. So I shopped as well.

Shopping with Annie had its perils of course. We enjoyed shopping at night, so we could walk the streets together in the shopping neighborhoods. Stores were always lit up and it was great people watching as well. I always walked on the street side with Annie because that is what a gentleman does. We could be innocently walking down the street having a conversation and suddenly I would find myself alone talking to myself. Sometimes it would take me several minutes to back track and find out which store Annie had dove into. Anything sparkly or sexy displayed in the window would draw her in.

In the beginning, when I would pick out clothing for her she would politely decline my choice saying it was a bit too conservative for her. After a few times like that, I decided to change tactics. I would choose some of the most scandalous outfits I could find. She loved it. Who knew? From that point on she insisted I shop with her, hang out by the dressing rooms and give my opinions. Nothing was too sexy or daring for her to wear.

One night when we were in Montreal she decided she wanted to go shopping for some personal lingerie. I said sure, I can just hang out at a coffee shop as they were on every corner in the old city. She said no, she had a particular shop she always went to for those items and I was to come with her. When we arrived I noticed the windows were all covered for privacy. I told her I didn’t think it was such a good idea for me to accompany her inside, as the clientele might not like a male inside while the ladies were trying on all sorts of things. She just laughed at me and said I was being provincial and she grabbed my hand and in we went.

I would be lying if I said I wasn’t embarrassed. There I sat on a comfortable chair while she tried on numerous things and would strut over to me to get my opinion. The fact that the sales women and other women trying on items didn’t even bat an eye that there was a male sitting right there in the open while they took items on and off while I desperately tried to focus only on Annie was distressing to say the least. She finally decided on her purchases and I said, great, we need to get out of here. She laughed at me so hard I had to join her. She was totally enjoying my discomfort in the whole situation and promised to give me a private show when we got back to the hotel. As we walked away, she whispered into my ear…think how much more you will enjoy it the next time. I just shook my head thinking how in the world did I get so lucky to have this sexy, sometimes fearful, sometimes fearless, sometimes powerful woman to look forward to being with the rest of my life.

Entry #9: Plan B

There was no Plan B.

Annie and I were both successful at what we did professionally, working independently most of the time.

By this point we were spending less and less time at our respective homes and traveling together practically every week both for work and to spend as many hours as possible together. We both knew that this model was not sustainable and we would have to make some choices.

Walking together through the various cities was one of those special things we enjoyed in the evenings. Yet underneath it all Annie was always apprehensive. She did not feel safe walking streets at night no matter how crowded and safe it might appear. As time went on, her sense of the lack of safety caused me to become more aware of our surroundings and as I began to worry for her myself, the enjoyment started to wane.

Deciding what to do next worked out quite naturally. We looked at all the cities that we visit regularly and put them into columns to decide where the safest and most positive vibe presented itself. Deciding to give up everything for each other was no easy path but we committed to it. We had talked multiple times about starting our own consulting business. We also discussed what would happen if we sold and gave up everything we had to move in a single purpose together for the future. It would be both difficult and painful, but we loved each other too much to not take the chance.

We decided on Montreal. We both love the old centre city with all the shops, restaurants, and bakeries. The fact that French was spoken almost everywhere in the old city made it the most romantic place outside of France itself. We both had contacts there and they assured us we could find an affordable flat in the most desirable area. Montreal was and still is the most accepting city I have been in and Annie felt safe there. Another positive is that we could actually get married there and live a normal life together. The U.S. did not allow our marriage at that time and the environment for us would not be welcoming.

Our business could be run from anywhere, and investing in and opening a business in Canada gave us favorable status for immigration. We put in motion a lot of the pieces to make it all happen and started the immigration paperwork that was going to take some time. We both started the process of notifying our employers of possible departure schedules and both were more than willing to work with us.

The plan was to make the move when Annie returned from her surgery in Thailand. She was having wedding bands made there at the same time by an artist she had researched. We would move to Montreal, get married, love and live with each other the rest of our lives. That was the whole plan. That was the only plan. There was no Plan B.

Annie went to Thailand and never returned. The only regret I have in life is not making that trip with her.

Entry #6: A Different Time

It was a different time in America when I met Annie. While we have come a long way in becoming a more accepting society, there is a long way to go. Today’s internet is so robust you would have a hard time not finding information on just about anything you wish to. Back then when we met, not so much.

On our third night (date) when she revealed that she was trans, I was so shocked that I was at a loss for words momentarily. I could not comprehend what that meant and asked her to explain. She said that while she lives her life as a woman and has since she was thirteen, she was born a boy. I said, that while I don’t know what that means for us, I don’t think it really matters. She responded that well…it will.

Annie was almost forty years old and had never had a relationship with a man and had no more than a handful of dates. She grew up in such fear for her safety and position in society that she closed herself off to everyone. Yet, on the first night we met, we both understood that we had stumbled into something that couldn’t be denied.

We met again the following week at a nice restaurant and the tension in the air was obvious. The few days apart had only solidified what we were feeling for each other. Our first kiss later that night was like a fire that consumed everything in the room. At one point I wondered if I would ever be able to breathe again. All of her fear and apprehension came to bear on the single moment she was so afraid of, but was desperate to experience. While we both wanted that final confirmation of what we felt for each other, all I could think of was that what I really wanted was to give her the love she lacked her whole life. I can’t recall everything I said, but remember mumbling something along the lines of “its only plumbing.” That night’s experience with Annie is something that I will never forget.

It just became better and better and more intense every time we were together until it ended.

There is no path forward to reimagine my experiences and passion for her with someone new. Deep down inside, I know that is my truth. She will always be the one and no one can take her place.