Missed opportunity from my teen years

Hi Everyone,

In the past few days I was thinking back to my teen years in high school in the late 70's. The girl I was dating at the time was telling me one night about the family was watching Phil Donahue and the show was about crossdressers and she was saying how cute the guys were all dressed up as ladies and she seem to not have a problem with crossdressing, At the time I was wearing pantyhose but not dressing otherwise. I so wanted to tell her I would love to CD, but I did not do so as I was worried about her and other's passing judgement on me. Looking at it in retrospect I should have told her and see if she would have helped me dress as a lady, Her and I were about the same size and I could have probably fit in her clothes.


Andy

Andy, I never had an opportunity like that, but I'm still hoping.

I had two girl cousins that wanted to dress me up, I was too embarrassed at the time to let them do it. It was in my early teen years and I had already been trying my Moms things on.

She also could have told everyone at school and made your young life considerably miserable. That was forty plus years ago. Leave it there, where it belongs.

I agree with Monica!

It's easy to imagine what might have been, but actually we are where we are. As someone who is in their 60's I often wonder what I would have been like to grow up trans if I had been born more recently. Would I have been able to dress as I wanted as a young person? would I have had the courage to do so? I don't know and I don't really see much profit in dwelling on it.

I'm not sure I had anyone in my past that I wanted to tell. The one person I'm glad I never told was my ex-wife. As she is a manipulator, she would have weaponized that information.

In my early years, I underdressed often..mostly panties and hose...sometimes a bra. I became serious about a girl in high school and, like you, the topic of CDing came up. She asked me if I ever dressed. The pause, thinking about my answer was enough. She smiled and said ?I think you do?, so I told her I?d thought about it. To my surprise, she told me it was OK, but I never did.

I was skinny with blonde hair down past my shoulders weighing about 135lb at 5'8". At the time (70s) it wasn't unusual to get mocked about long hair by being called "girl" in stores etc. I could have dressed and passed in a heartbeat. Just didn't know about CDing.
Now at 66, I can't remember the last time I could see my own hair without a mirror. I weigh 30lbs more and am definitely old. I couldn't pass to save my life.
If the internet and the vast amount of information about CDing and even Transgender potential was availale back then, I'd probably be a woman by now.

I remember donahue having CD episodes in the 90s but I didn't know he had them in the 70s. But, in the late 70s I had a GF that told me she was bi within the first couple of weeks of our relationship. So I felt that I could tell her about my crossdressing and she was into it!

She was a hairdresser and changed my hairstyle. She also had me dressing (not crossdressing) a bit effeminate in public and one of my friends said she was turning me into a fairy! Never had another GF like her even though I've been out front with others regarding my CDing. Anyway, we were together for 1 1/2 years and the relationship ended for a couple of other reasons.

Andy, you blew it! LOL

If I had the internet, with all the info and resources, when I was in my teens (late 70's, early 80's) I probably would have transitioned or even had SRS by my mid 20's

Monica nailed it!:thumbsup:

Judging by mine? Those teenage years r best forgotten!:doh:

Trust me I am not losing any sleep over it these days, just makes me wonder what might of happened.

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That is one of the big reasons I did not tell her back then.

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Oh trust me I know I blew it! LOL

Yes, there were a couple minor incidents. I did not want to tell any girls--I had enough problems finding girls that wanted to go out with me.
However, there was an incident when my roommate's girlfriend needed a ride. She told me about dressing up a boy a year ago to go to a women's night at the movies. However, I think my roommate had somehow discovered my stash of magazines. Probably he told her about his suspicions. I almost agreed to going to the movies dressed--she was about my size--however--she was a college student. She did not have any dresses on campus. Jeans only. If only.

Yep -- Monica is right about this! Just too many "if's" in that situation: if you had told her; if she was accepting; if she might have been willing to help you; and the big one already mentioned - if she kept your secret. You and everyone else know all of this, but it does make a fond memory to think back upon what might have been. At the risk of outing my self as a fan, I think there was a Garth Brooks song that went into "memories of an old high school girl friend" though I can remember some of the refrain, I can't remember the title - the end was that when they met up later, neither felt the same way they had those years ago.

It still would have been a crap-shoot. Saying the guys on Donahue are “cute” is a lot different than finding out your boyfriend is one of them.

I wish the internet and transformation/makeover places existed back in my teens (80’s) I would’ve loved to have seen what I’d have looked like.

Halloween seventh grade. Before that I had an inkling that I wanted to try wearing feminine clothes but I don?t think it was a real thought or desire. Then my girlfriend and her friend decided it would be fun to dress me up and go trick or treating. The idea both terrified me and excited me. I let them dress me up in a blouse and plaid skirt, stockings and low heels. They did my make up and fixed my longish hair. I was playing it off like I was not enjoying all the fuss but inside I found it exciting. We spent several hours trick or treating. A wonderful night except when I tripped in my heels going down stairs and tumbled down the stairs in a most unladylike fashion. Coincidentally, it wasn?t too long after that I started trying on some of my mother?s things. 🤔