In 1999, I was off to college, and while I previously posted about some of those early experiences, I did not mention sharing my crossdressing secret for the first time. The reason I chose not to include it in The College Years: 1999 was that I felt that it needed its own entry.
I made a really good female friend during my first two months at college. We spoke frequently and became very good buddies, so one day I decided that I would try to share this with her and hope for the best. Worst case scenario, she wouldn’t talk to me ever again, and I would lose her friendship. This was a huge risk that I took, but she didn’t know any of my family or other friends so I felt that I was not jeopardizing my personal privacy. Well, not only did it not ruin our friendship, I ended up benefiting even more from this decision.
I remember being at my parents’ house, upstairs in my bedroom, with the door locked. I called my friend (let’s call her Nancy) and she answered. We spoke for a bit, but soon I dropped the information bomb on her. Now I can’t recall exactly what I said, but I believe that we started talking about shopping and I mentioned that it would be nice to buy some girl clothes and wear them. She asked me if I was serious and I affirmed.
As the conversation went on, I told her that I had actually dressed up like a girl before and had been doing it for a while. My heart raced as I spoke, because this was my first time opening up to a friend about my crossdressing. She actually thought it was cool and interesting, luckily for me. During our talk, she offered to take me shopping for some womens’ clothing.
About two or three weeks later, she actually came through on her incredible offer. We drove together to a mall, walked in, and began shopping. Shortly after, she figured out my size just by looking at me and making an estimate. Or so I thought, because at the time I wasn’t aware that girls could tell each other’s sizes so easily. Nancy and I ended browsing several stores, taking our time to browse, all the while having a fun time. I picked up a few items, all of which were purchased without trying them on. Although I might have been able to, I was simply too nervous and anxious to even attempt entering a fitting room with those clothes. Anyway, it didn’t matter at the time, because to me, just having a small wardrobe was a treasure.
I believe that I had already adopted the Jessica persona by then. This otherwise ordinary Saturday turned out to be a very key 24 hours of my life. All those years of shame seemed to simply disappear during that wonderful shopping trip. As a crossdresser, being accepted, supported, and even encouraged is paramount. Just like anyone else, we long to feel normal and engage in activities normally reserved for women.
These events happened almost ten years ago, and I sadly must admit that as time has passed, this epic adventure crept into the backlog of my memory. In other words, I sort of forgot about it. Luckily, I have this outlet to share my feelings and experiences with you all. To ‘Nancy’, if you ever read this entry, I hope you know that what you did in supporting me was very much appreciated. You played a meaningful role in my life and helped someone who was very scared, confused and lonely.
I wonder if any of you out there have had similar experiences. If so, I would really love to hear about them. Feel free to leave a comment or send an email. Until next time, take care everyone!
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