Better Late Than Never – Part 1

My journey to a complete and fulfilling life has decidedly run through Crossdresser Heaven and Harrisburg, Pennsylvania. Who knew? The power and promise of an event like Keystone is perhaps unmatched. It has offered many of us an opportunity to embrace our true and authentic selves. Crossdresser Heaven has proven to be an outlet that has allowed me to cultivate my community. It’s taken me decades, and a lot of fits, starts, and some pretty life- changing events, to get here. I am just glad I made it.

Getting to Keystone goes back a long way and telling my tale here — one that may not be too dissimilar from others who have come to this space — may serve a broader purpose and help another who has yet to come to terms with their own identity: Cross-dresser; Transgender; Gender-fluid; Gender non-conforming; Non-binary. Does the label matter? I’m at Crossdresser Heaven and Keystone with friends and just being here, without the fear of judgment, ridicule or any other form of negativity is enough to make me want to pull out a chaise lounge, pour out a nice cocktail and just sit and breathe in the peaceful bliss of self-worth, confidence and finding my people.

Carrying what felt like a 4-ton sack of bricks for four decades is not easy. To carry the load all alone, and feel somehow that I was doomed to a lifetime of being just exhausted and judged as an outcast, was daunting, even when I did not believe it was. I never considered it burdensome or painful until I actually started to slowly reduce the weight one brick at a time. Looking at it now, is it any wonder I got sick over it?

Dragging around my burden as I had for so long, I have come to understand that it put my very existence in jeopardy and I wasted 40 years sprinting, running and racing until I could just no longer outrun my very self. I finally stopped in the past few years, and I found myself here at CDH and the Keystone Conference! Mercy arrived in community.

A Similar Story?

This may yet prove to be a very common narrative, however I still feel the need to share my experience here in its entirety.

Thirteen years old, and trying on girls’ things for the first time — I had no clue how, where or why there was such a burning, deep-seated need! And it was a need; not just a casual, “I wonder how it would feel if…” kind of sense about it. Crudely presenting at first, I masked the entire experience in teenage-level fetish. I called it a ‘phase’. Looking back 40 years, I was clearly looking for a way to cope with something I did not yet fully comprehend, accept or acknowledge. Fear proved to be a powerful barrier.

“…I am the only boy in all of the world that is doing this. The only one! And look, I’m just messing around. I’m not gay and I don’t really want to be a girl, right? Yeah… That’s it. It has to be. I will simply grow out of it…”

There. See? Simple. Easy. And so the secret was born.

Except my laziness crept in pretty early on in the process, because what was happening was hardly a rarity. I was not feeling this ‘deep need’ once a month, or even once a week. It was every day. And sneaking in and out of my sister’s room — even though she was away at school — was annoying me. It felt worse to be sneaking into her room at all, and to do so for the purpose of taking items of her clothing — mortifying. Plus, the floors creaked and I did not want to tiptoe in to her room twice a day in quick succession — once to get the items, and once to return them — while my mother was home. I did not need to hear the dreaded, “what are you doing in your sister’s room?” Bellow from below. After a short time, I just kept the stash — and the stash just kept growing — under my bed.

How brilliant! I’m keeping this pile of all kinds of garments under the bed my mother insists on making every single day. “No chance of her finding it…” Hard to believe the C.I.A. passed on my application.

Throughout the rest of my middle school and high school years, this ‘phase’ continued. Slowly it became more adventurous. I’d spend more time in my crude, basic presentation. All the while I presented a different person to the world. It was a standard, suburban, middle-class upbringing in the 1980s. I was a typically awkward kid, but I had the girlfriends and buddies that I hung out with. I struggled through most of it — trying to find my own niche and way to fit in. I’d like to believe that by senior year in high school enough of us had grown to the point where the bullying stopped and the plans of life were taking shape. College was calling, and I was on my way.

I attended art school and for the first time since the ‘phase’ began, I thought perhaps I was right and I had ‘grown out of it.’ School was intense, and my schedule provided zero time for anything other than classes and homework. Girlfriends during those years took up whatever free time I had, and my new friends took up the rest. I found a big part of my voice in those four years, and while I really seemed to see the ‘phase’ diminish, it never really fully went away either and anytime I returned home, it was all waiting for me.

By the time school ended, and I began living on my own that first summer; the ability to dress while home became more present, and more consuming than it had been prior to college. I was on my own, and given the choice of how I wanted to present around my own place, my choice was decisively female — at least a good part of the time.

It was not too long before I would begin pushing out into the late-night hours for a long walk or drive. Thinking back on it, I must have looked ridiculous. By this point it was a mishmash of clothes and things to try and look the part, but it was as if Dr. Frankenstein had pieced together some kind of bizarre cross-dresser monster. I will spare the details, but beginning to make a public appearance — even if in a remote area late at night — was a true indication that this was no longer really a phase. Perhaps I allowed it to become a fetish, but it was clear that it was here to stay.

The following two tabs change content below.

• Bio
• Latest Posts

Andrea Smith

I have been someone who has struggled a very long time with my gender identity and have only recently come to accept my truth. It is liberating and wonderful, and also frightening. I am hoping that as I continue to accept more and deny less, my authentic and more importantly complete self will emerge. I live in the NYC burbs. Enjoy photography, museums, history, old tv shows, movies and cooking.

Latest posts by Andrea Smith (see all)

• Better Late Than Never – Part 4 - May 10, 2025
• Better Late Than Never – Part 3 - May 3, 2025
• Better Late Than Never – Part 2 - April 29, 2025
• Better Late Than Never – Part 1 - April 19, 2025

Subscribe To Our Newsletter

Join our mailing list to receive the latest news and articles from Crossdresser Heaven.

SUBSCRIBE!

You have Successfully Subscribed!

We hate spam too, unsubscribe at any time.