Early Years

A Few More Firsts

chicago couple date hug
Photo by Snapwire on Pexels.com

As I moved to Chicago, I experienced many new things.

  • First time living in a big city
  • Auditioning for dance companies
  • Riding public transit rather than driving
  • Becoming a fully certified Pilates instructor
  • Learning how to not get blown over in the Chicago wind
  • And for the point of this blog, my first real relationship

I met *Jay sometime during the fall of my first year in Chicago. He was the roommate of the boyfriend of one of my best friends. We met at a dinner one night and hit it off. Things progressed from there. I remember he was into some sort of martial arts/fighting thing for workout and had signed up to participate in an actual fight. Maybe it was actual boxing? My memory on this is a little fuzzy. Anyway I went to see his match with a few other friends and everything was going great until he was suddenly down and out with an injury. It turned out to be an ACL tear. Great. I finally find myself a guy and he gets laid up with crutches and a giant brace on his leg with an impending Chicago winter. Thanks universe!

Jay was a good sport though and once he became a bit more mobile, we still hung out quite a bit although we didn’t go out on many dates. He did brave his way to WV for New Year’s and attended a friend’s wedding with me and became the first guy I ever brought home to meet my family. When a giant snowstorm hit Chicago and had everyone buried under mountains of snow for at least a week, he trudged his way over to spend part of the time with me. Seeing how a majority of our relationship was spent cuddled up on a couch or in a bed due to injury and ridiculous Chicago weather, Jay was surprisingly patient yet persistent with allowing our relationship to progress at my pace. He was respectful of the fact that I was less experienced in the physical part of relationships and was willing to take things slow. He was more than willing to give out pleasure and make sure I was satisfied. Now before you go thinking I was just lying there becoming a pleasure whore, rest assured I put in the work to return the favor. He said getting him close was a compliment to me and he would generally help himself over the finish line. His pierced genitalia made the whole process a little awkward anyway so that was kind of fine with me. Surprise! Yeah that was a first that I did not expect to ever experience.  

A few months into this relationship, I decided I was ready to give up my V-card and enter the big leagues. Luckily, this choice did not disappoint. I gained a lot of confidence in my sexuality from this relationship and although I wasn’t exactly looking to go jumping into bed with any guy who came knocking, at least now I knew what I was doing. I still put value in building the relationship first and saving the prize for the right people. Or so I thought.

After about 6 months, where we saw Jay re-tear his ACL during recovery while walking down a slippery Chicago sidewalk, he ended things with me rather abruptly. One day he came over to my place with a couple of random things he had of mine. His explanation was simple- “I woke up this morning and you weren’t the first thing I thought of. In my past relationships, things started going badly when that happened.” Oh well that’s interesting. Thanks for making it a discussion or giving me any say in the matter. After the shock wore off, I realized this was ok in the long run. Although I will always be thankful for the experience I gained from this relationship, I sort of already knew that I wasn’t in love with him even if we did say those words.

Until next time…


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