what are some missed opportunities you wish you made

[Heather2die4]

Paula: we all regret not being honest. I know I do. I came out to my mother at 23, a full ten years after I started cross dressing. Missed opportunity? I had the chance to travel in Asia which has a long tradition of acceptance, even celebration of different lifestyles. I wish I would have brought my femme wardrobe. Well, it wouldn't have fit in my backpack but would have been fun to live for awhile as a tall young woman and respected in the community.

Regrets? The Society for the Second Self tri-ess.org has a partners' bill of rights. Basic common sense things like, she has the right to expect that I won't try on her clothes without her permission, to not have crossdressing take over the relationship, etc. I wish I had seen that sooner. A few times I have entered a girlfriend's lingerie drawer. I regret that. I also regret that my crossdressing has been a solo activity. I'm on this site to change that and build community.

[tinadee]

Years ago when I was still closeted, I got my hair done up pretty by an understanding stylist at an out-of-town beauty shop that I frequented in guy-mode, and then I visited a woman's clothing store to look around, but not intending to purchase anything since my wife was unaware. A female manager walked up and said another man talked to her recently about purchasing women's clothing, and so the manager was considering hosting an invitation-only evening for guys who want woman's clothing. She gave me her card and said to call her. I never did. Foolish me. I've checked recently, and that store is now closed. Seize opportunity. Opportunity is like the tuft of hair on a balding man's head. Grasp it now, before it is gone.

[Joanne86]

After seeing the initial post I have wavered on what would constitute something that may have been any missed/lost opportunity type of deals. Of course I am young enough, in my early 30s, that I can still capitalize on opportunities of the future but doesn’t mean there haven’t been missed opportunities in the past.

I would say that maybe one aspect would be not taking the opportunity to dress more. Part of that though is my limited wardrobe both of the past and present and limited funds to purchase those items. Buying women's clothing is just low on the priority list of shopping. I had a long term relationship with a girl who didn’t outright object probably because it didn’t come up that often either in conversation or actual dressing though I have a strong feeling she wasn’t thrilled. But I have been single for a good while now and even though I live alone I really don’t engage in dressing as much as I maybe could or even should. The tricky part is defining should. So I could say I there may be many missed opportunities I could have had in my 20s but didn’t know about.

One really out there missed opportunity might not deal with actual dressing per se but the mentality and that is talking to a psychologist/psychiatrist especially closer to my late teens and early 20s. I really wonder if that would have changed things. Back in my teens and early 20s I didn’t know about transgender, the internet was not nearly what it is today when I distinctly remember being interested in women’s clothing which was before becoming a teenager. That and the idea of being transgender has been on my mind more in the last few years so it clearly begs the question, what if? What if I had been able to learn more about gender identity when I was yonger? What if I had talked to a psychologist/psychiatric when I was younger? What if I had known more crossdressers or more resources about crossdressing when I was younger? How would all of this have affected my path? Sure there really isn’t much stopping me from doing those things now but we are talking about missed opportunities. There are plenty of stories out there of people in their 30s discovering more about themselves and coming to terms with things like identities. I just partially look at it as it might have been better in my 20s compared to 30s especially if it concerned being transgender. If I was able to solidify things more back when I was younger there is a chance I may have enjoyed life more.

[Kate Jennings]

For the most part I acted on what I wanted to act on, but, I do have one glaring regret.

I had a girlfriend who was very open sexually, into costume, etc. One night she said "If a couple wants to experiment with things like crossdressing I think that's cool". I was in a "down mode" period in my dressing, at that time, I will always regret that I didn't jump on the chance. We broke up a few months later.