Over the St. Patrick’s Day weekend in 2006, I traveled to Baltimore, Maryland to meet a friend, Andy, that I had been chatting online with for some time. He explained to me that the weekend was a great opportunity for me to visit because it would give me a chance to see a leather titleholder contest – the Maryland Leather Sir/Leather boy contest. It was an all-weekend event, so I needed to make sure I had enough time off planned.
I was excited to get the time off and a plane ticket booked to go up there and see him for the first time. I had learned that he was a transman, and so I wanted to understand more about what that meant. I was 22 years old at the time, so I did not know much about gay culture, much less leather or any other cultures associated with any alternative lifestyles.
The weekend was an amazing time. I still remember so many of the vivid details of the fantasy scenes that were put on by the contestants competing in the contest, and also many of the things that happened outside of the event itself. Of note, I remember Andy telling me on the last night of the contest after the winners were announced that he had seen me stick around him pretty much the whole time we were there.
I hadn’t realized it, but I guess I had been doing that because it was new territory and I didn’t know the surroundings or the people. He challenged me to go talk to other people and not come back to find him where he would be sitting until last call. I swallowed my anxieties and went up to one of the contestants who was in a group of people, chatting. Quickly, I was able to join in on the conversation as I picked up that the conversation was idle chatter and not a personal one.
I explained that it was my first experience in the lifestyle, and that I had found it quite interesting. The contestant and several of his friends had lots of questions that they asked me, and we really had a great conversation. We talked about some of the nomenclature and relationship dynamics. One of them even flirted with me, which really caught me off guard. I blushed, and thanked him for the kind gesture.
Before I knew it, the evening was drawing to a close. We went to our established breakfast joint afterward, in full dress leather, mind you (except for me), and I felt like something amazing had happened. Andy describes my attitude as like a kid in a candy store with free reign. The trip home to Tampa would happen all too soon, though, so I knew that once I got back home I’d have to find something here.
My initial searches in the area found the Tampa Leather Club, and Club 2606 (which I may affectionately refer to as 2606, or just 06). 2606 was a Leather/Levi bar at the time that featured the nice dark seedy corners that most expected from a leather bar when they were going there to have some fun for the evening. On many a weekend night, I found myself buried in the corner of their upstairs lounge so that I could watch all the festivities. One could barely see what was going on, because there was only a single red incandescent light bulb illuminating the area, but the noises made up for it for sure!
Membership with the Tampa Leather Club and going to the 06 helped me get some friends that I am still close with to this day. The first Sir that I ever served and my best friend in leather were both forged here. I also got to walk with the Club in St. Pete Pride. It was my first ever Gay Pride parade, and it was an amazing experience.
As I explored the lifestyle, I very quickly realized that I enjoyed masochism. Sir Tom took a flogger from the 06’s shop and used it on me one evening, and I really enjoyed it. He taught me how to stand safely and how to safely communicate with Him with hand signals since the bar was loud and patrons would often carry on, egging Him on as the scene unfolded (which was often fun, sometimes ridiculous).
Years would pass, and I will continue to chronicle how things went from then in this blog, but this is how the journey began.
I’ve not yet decided if I want to have comments here or on a social media site. For now, they are disabled, but I will enable them at a later time.