Missed opportunities with someone.

[JMO2]

This is more for my benefit than the forum. I will state that right off quick.
When I was in my first year of High School I was proud enough to know someone who I really liked and admired.
At this time I was crossdressing and quite new to all of it and had no clue as to why I was crossdressing.
She was pretty and she was "too good for me". As they would say.
Well the reason I have to say "too good for me" was because she hung with the popular crowd and
was too pretty to be classified in the same category as me.
Well I was just learning what crossdressing was and there were too many rednecks in my school.
So rather than do or say anything I let things go and was her friend.
One day she came over to my house unannounced and sat down on my bed
to spend some time talking to me. She sat extremely close to me. Almost sitting
on my hip sort of. I moved over. (the thought ran through my mind "I'm a crossdresser. I cannot
even if I wanted to date you. You are in a higher class crowd than me.")
I got up to change the record on the record player to try to sit a little further away from her.
She again moved over against me - sort of.
Years later (I think around 35) there are regrets setting in that I want and need to push out of my mind.
The main reason I brought all this up is because - had they known what crossdressing and Transgender is
and had delt with it back then - would have things been different?
Look how far we have come since then? We now have groups for both.
We have a better understanding of what causes some of it.
I have a wonderful SO and a great 10 year old son and yet my thoughts
keep going back to then and what if...............
Has anyone else had any experiences similar to this?
How did you deal with them as far as crossdressing went?

[JustJoni]

JMO2,

I have things/thoughts like this sometimes, but I can sort of lay them at the feet of the fat that my first wife passed away, and I am now remarried to my high school sweetheart. I would not change having my two wonderful children with my late wife, but I (and my wife) still sometimes 'wonder how it would be different today if we hadn't broken up' as it were. I think as we pass into middle age, the thoughts of what we might have done different do loom larger.

Now, I crossdressed then, too, but my current wife (then my girlfriend) never knew. had we been together longer, I might have come out to her then as I trusted her deeply. Indeed, before we were married last year I did come out to her, and she said some things from our high school romance suddenly clicked knowing that this is who I am...now that also makes us say 'what if I had confided in her then'.

[docrobbysherry]

People think and do things quite differently, JMO. At age 17, I found myself broke, alone, and 1000's of miles from home in a foreign country. At that moment I resolved to never again pass up an opportunity I mite later look back on with regrets.
Not only has that policy worked my entire life, it gave me the courage to ask for money from a stranger so I could start home the next day!

And, other than my pre 17 high school timidness? I can't recall letting any opportunities worth mentioning pass me by since then. No matter how bad my teeth were grinding, hands shaking, and perspirant was failing me!

[ClosetED]

I had a few missed opportunities as well. In college, I had a girlfriend for my final year. A girl in one of my classes was a '10' - gorgeous, intelligent, funny and she gave me her number. But since I had a GF, I stayed loyal. During residency, I was set up with a girl who the male friend said I was just the type she was looking for in a guy. Turns out she was lesbian and was hoping to change and a sensitive guy was what she hoped would let her overcome the sexual trauma she suffered thru and was unable to have intercourse. When she opened up to me, I shared with her that I was CD and hoped she would dress me. However, to fill her hopes of being with a guy, she did not. She ended up leaving me for a woman. But I always wondered if I had pushed for her to dress me and treat me as a woman, what might had that led to.
Hugs, Ellen

[Leslie Langford]

Yes, this was likely a missed opportunity, but what exactly was the "missed" part?...opening up to her as your "friend", admitting that you were a crossdresser, gauging her reaction, and then hoping for a sympathetic ear along with acceptance...or else letting nature take its course in what was likely a sexually charged moment despite your insecurities around your crush being "too good for me".

If it was because you were confused about your sexuality, were afraid that you were actually gay as a result of your crossdressing proclivities, and didn't want to lead her on and potentially let her down at some point when the "truth" came out, that might have been understandable under the circumstances.

Hopefully, you realize by now that your gender identity and sexual orientation are two distinctly different entities, and that the two are usually mutually exclusive. Looking back, there is no valid reason you couldn't have had a heterosexual relationship with your female friend - at least from your perspective. On the other hand, you being a crossdresser could have totally freaked her out, but that is a whole different issue and would have had more to do the way males and females were socialized back in those days as opposed to it strictly being a matter of sexual orientation for either one of you.

My take on what you have written here is that you apparently felt that one reason she was "too good for me" was that by being a crossdresser, it would somehow have made you unworthy in her eyes and a lesser human being as opposed to having some other, more "socially acceptable" - albeit self-imposed - failing. Hopefully, you have learned enough about yourself since then and are in tune enough with the way the world now sees gender and sexual diversity that you no longer stigmatize yourself in this way. You (and all of us here) are just as worthy as human beings as the next person, irregardless of the fact that in our particular cases, wearing women's clothes happens to turn our collective cranks.

When all is said and done, how is this passion of ours any different from, say, being a golf addict, enjoying restoring vintage cars, being a Civil War re-enactor, participating in cosplay, being a Trekkie, or pursuing any number of other similarly pleasurable - yet "manly" - pastimes, only because society arbitrarily labels some of them acceptable and others less so, and for no real logical reason.

And truth be told, how many of these popular, attractive, "too good for me" young women eventually ended up with some slick, macho jerk because she was socially conditioned to do so, only to find out in due course that her Prince Charming was nothing more than a lying, cheating alcoholic and abusive womanizer who couldn't hold a job, and with her eventually ending up as a single mom to get away from all this drama. Maybe marrying a - gasp! - crossdresser wouldn't have been so bad in comparison...

[Allison Chaynes]

As far as a romantic situation, no, at least not as far as CD is concerned. Now do I think I should have reached out to certain family or friends past that might have been supportive, maybe.

[Aunt Kelly]

It's fun, sometimes, to speculate on "what might have been", but I would never waste time or energy on feeling regret about choices not made.

[Trione]

At this point in life if some CD came on to me I would embrace it and go for whatever

[Tracii G]

No sense in living in the past or thinking "what if" because it didn't happen.
You married a different person and the rest is history.
Be thankful for your marriage and your Son because thats what is important.
If I dwelled on all the things in my past I would be in a very dark place.

[JMO2]

Thank you for your very caring and meaningful answers.
This actually puts my thoughts more in perspective.
It actually makes me understand why I did what I did and
how it relates to now.
Moving on from this has been an eye opener in several ways.
Both mentally and physically as well as emotionally.
Both having an SO and a son has kept me grounded.
I don't stay up at night and think about the what "might have been".
but it did bother me from time to time by the questions I had.
I couldn't have gotten a better answer if I had seen a therapist.
Thank you and I am grateful for that.

[Tama]

At least my opportunity was a well timed "early warning" alarm. When I was about 18, my girlfriend at that time left a skirt on the bed, and in a moment of "what if..?" I tried it on and She walked into the room.. OH MY!! The shock and horror of such an act! "take that thing off right now!" was the shot in the heart I felt but, at very least I knew this phase was a DADT. It lasted 6 more years and died off, and my wife now is fortunately very supportive so, this was a good thing, just didn't know it way back when. Dodged that projectile now didn't it?

[kimdl93]

I can't think of a single missed opportunity. That doesn't mean there weren't any. It just means that given my limited knowledge (i.e. Prejudices and misinformation) and generally oblivious nature, I wouldn't have recognized an opportunity if it walked up and bit me. Thank god, you didn't ask about regrets...I have so many of those.

[Periwinkle]

I wish I would've put myself out there more in high school. Not only was I going through my 'super manly' phase, but I was hesitant about pretty much everything. I would overthink things and give myself excuses as to why doing certain things were a bad idea.

I would've liked to have been an entertainer at this point. Not someone famous, but someone who could make people happy at least. I held myself back from things like choir and drama because I was ashamed of my squeaky voice and feminine features. Sometimes I feel like I could've done it if I had just been more comfortable with who I really was back then and gotten the interpersonal experience I would've needed to do what I like the most for a job. I like my job at McDonalds a lot, and I feel like I've learned a lot from it. But sometimes I think being a singer or an actor would've been pretty great.

[Dana44]

Ah, think about the past. There was a one pretty girl that like me but I passed her and married another girl from another town. It was during a reunion that she told me. Lost opportunity but the past we cannot change. We ha a nice talk and it was great. However I lived far far away and had my own life with another woman. In fact I had many women and I guess this feminine side of me was too much for many. But I had a lot of long term partners but no one who ever loved me for me. When I retired well semi retired. I found one that love me for me. So a missed opportunity may be the best thong that happened to me. Anyway we cannot change the past..

[sometimes_miss]

So many things I would change were I to re-live my life again. But it won't help. So I don't dwell on it. No sense beating myself up about what could have been; there's still a lot of life left to live, and it's better to focus on the things I can still accomplish instead of sitting around feeling bad about the past.