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Thread: Biggest missed opportunity

  1. #1
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    Biggest missed opportunity

    I mentioned in another thread about a girlfriend I had when I was very young. She lived in a big city and had some gay neighbors that liked putting on drag shows at their Saturday parties in their apartment. She hinted around that she wanted to enter me in the show.

    Never came to pass, too young and insecure to get in a dress with gay men, even though my girlfriend would . . .reward me, if I did.

    Always wonder what that would have been like.

    What missed opportunities have you had?

    SJ

  2. #2
    Aspiring Member SaraLin's Avatar
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    The one that always comes to mind is the time I was with a lady friend shopping for her wedding dress. One of the ladies working in the store asked me if I'd like to try something on.
    I was dressed male at the time, and I declined. Too timid to say "I'd LOVE to!"

    Oddly enough, when we went back to pick it up, I was dressed femme this time and the same offer was NOT extended.
    I'm not sure what to make of that.

  3. #3
    Member Mermaiden's Avatar
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    Way back in college my then girlfriend, now wife, suggested I could wear her panties when my underwear was all in the laundry. I should have run with it - if only I?d known my true self!

  4. #4
    Aspiring Member Violetgray's Avatar
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    I was cast in a low-budget movie about a group of goth squatters. The costume designer for the movie took one look at me and decided that she was going to go full female with my look.

    But the movie never ended up getting made

  5. #5
    New Member NatalieR's Avatar
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    When I came out to my best friend, I told her I had a dream that I was a bridesmaid in her wedding. She said "You should have told me. I would have asked you!!"

  6. #6
    Gold Member alwayshave's Avatar
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    My first long term GF, who di don't know I dressed, once tried to put a slip on me while were in bed and I balked. Too bad.
    Please call me Jamie, I always_have crossdressed, I always will, "alwayshave".

  7. #7
    Resident Polymath MarinaTwelve200's Avatar
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    Back in the early 1960s It turned out that ALL of my guy friends were dressing up as GIRLS for our Halloween Trick or treating outing.---I could have asked my Mother to do ME up too--and she would have joyfully done it, but I chickened out and dressed as the "Grim Reaper instead. I supposed I feared my "secret" would have somehow got out. Foolish ME.

  8. #8
    Miss Conception Karren Hutton's Avatar
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    My mother was always telling me that I was supposed to have been born a girl and on a number of occasions she had volunteered to dress me up as a girl for Halloween. Wish I had taken her up on it. Strange enough about 5 years ago my HR rep at work told me I had an issue with my gender at Social Security. Apparently my mother had marked it F on my application and it was had been that way for 60 years. HD to get it changed back to an M so my pension payments would be correct which was a pain In the ?&$@! Might have been easier to leave it an F and gone for gender reassignment!

  9. #9
    Super Moderator Raychel's Avatar
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    Back when I was a young boy. Probably like 8 or 9 years old
    I was at a friend's house. He wasn't home. But his sisters and super good looking mother was. The 2 sisters wanted to dress me up as a girl.
    I was way to embarrassed to let them do it.
    But we all know how much I would have loved that
    my sister's reply when I told her how I prefer to dress

    "Everyone has there thing, all that matters is that you are happy, love what you do and who you do it with"

  10. #10
    Aspiring Member Heather76's Avatar
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    My biggest missed opportunity had nothing to do with cross dressing; but, may have had an impact on my being more inclined. When I was 18 years old I was staying overnight with a work associate who was 25 or 26. He made a no-nonsense sexual pass at me. I left his apartment and went home. In 1963 I had a 100% closed mind about sexuality and male/female behaviors. Maybe if I had accepted his invitation I'd have been more open minded a lot earlier in my life and not waited until age 74 to start dressing and coming out to my wife. While she doesn't like it and prefers not to see me wearing, she does accept it as a fact of my life.
    It's never too late to enjoy a happy childhood.
    Live each day as though it's your last 'cause one day you'll be right.
    I'm finding the more feminine side of me...and I ❤️ this adventure.

  11. #11
    Silver Member Sometimes Steffi's Avatar
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    I had been working on my car, not very successfully. One of my neighbors came by to see what I was doing. He said I needed a socket wrench to use instead of my box wrenches and he let me borrow his socket set to complete the repair. When I finished, I brought the socket set back to him, and he invited me in for a beer or two.

    After talking, and maybe two or three beers in, he put his hand on my knee. Even through three beers, I finally understood what was happening.

    Arooga, Arooga, Battle Stations !! Battle Stations !! This is not a drill!!

    I quickly and safely made my exit, but afterwards, I wondered if he had some femme clothes that I could dress in. That's when I was convinced that CD equaled gay, and I was somehow a CD who wasn't gay.
    Hi, I'm Steffi and I'm a crossdresser... And I accept and celebrate both sides of me. Or, maybe I'm gender fluid.

  12. #12
    Gold Member Crissy 107's Avatar
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    When I was young I had two girl cousins who wanted to dress me up, I was too embarrassed to let them do it. I still do regret it
    Crissy

  13. #13
    Aspiring Member Trish's Avatar
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    I got lucky, I didn't miss the opportunity when my then girlfriend wanted me to try on a dress. I did, we are married, and I have more dresses in my closet than she does.

  14. #14
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    I remember two. Both occurred during the first year of our marriage. The first was when we were lying on our bed, and for some reason my wife decided to put her bra on me. I immediately got very amorous, which seemed to alarm her, so I backed off, missing an opportunity to open up to her about my attraction to feminine garb. The second was the night we happened to be watching the Carol Burnett show in which she did the skit where the male cast members had a leg contest in pantyhose. I considered saying something like, "I'll bet I could have won that contest", but I was deterred by her comment that the skit was "disgusting". It took another 20 years after that before we reached an initial DADT agreement, and only through her repeated discoveries of my stash.

  15. #15
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    More recently I probably had the opportunity to open a dialogue but I blew it. It could also had been a case of wishful thinking on my part so I did not pursue the opportunity. My wife and I are in a deep "Don't Ask, Don't Tell" marriage. We had "The Talk" back circa 1983 which included all those nasty statements that are emitted from the mouth of most women; "I I had known I would not have married you!" She also told me she wished she had not shared her "secrets" with me because it would have made it easy to just walk out the door. She said it would have been two-faced to just walk away. Throughout our marriage you can guess whose secrets have had the most significant consequences. It has not been me. Anyway, to get to the point.

    About three years ago my wife was cleaning out the back of her side of the walk-in closet. There were scores of sexy nightgowns that no longer fit her. (Sigh!) She thought about donating them to Goodwill. Nope. I suggested a local charity shop; American Cancer Society Discovery Shop in the Proctor District of my small city. It is operated/staffed by volunteers and price garments reasonably. I have issues with Good will. Anyway, we ended up washing all the garments and pressing them before donating. My wife told me, if there was anything in the pile I wanted to take it. I was not prepared for that offer. I did end up keeping a white peignoir that I had bought her as a wedding gift back in 1971. I did not know anything about women's sizes. It was a medium. It swam on her petite body. One night she found me trying it on in the kitchen. She asked why? I told her I like the feel of the nylon which is true. We ended up buying myself a midi length pink peignoir which I still have and sleep in and a black ankles length gown which is long gone. I missed the opportunity to break that thirty year silence.

    More recently my wife and I were driving home from a Christmas shopping trip and were discussing transgender issues. I cannot recall how we got on the subject. The gist of the conversation was some people are just "born that way." She has a second cousin who is a transman who recently gave birth to a baby. She also has lunch once a month with a lesbian friend who went through the routine of marrying a man and having a child before breaking the bondage of societal norms and expectations.

    I did not jump at these "openings" because I feared her acceptance perhaps came with that added "Not in my back yard!" After fifty years of marriage my wife and I know where we both stand when it comes to our marriage. If there was some enhanced degree of acceptance I wish she would have just come out and said something more encouraging. I just did not want to say something and get cut off at the knees.

  16. #16
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    Me and my wife, at the time, were in a adult novelty store. I had never told her about my urge to dress. As we made our way through the store she had picked out a couple lacey things then turns to me and says " pick you out something".. I didn't know what to say or how to even respond. I was kicking myself walking out the door empty handed. Atleast her bag was full.

  17. #17
    Aspiring Member MonicaPVD's Avatar
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    I attended university far from home and spent a considerable amount of time dressing in public as a woman, and even dating as such. That was the best opportunity to transition but I chickened out. My family is very conservative and the only trans people I knew of lived on the fringe of society and certainly did not live well.

  18. #18
    Exploring NEPA now Cheryl T's Avatar
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    I was about 11 and at my aunt's. Cousin and I were fooling around wearing my aunt's clothes and she found us.
    She pulled me aside and said if I wanted to wear her things just ask and she would help me. I was too scared everyone would know and never asked. Now I always wonder, what if??
    I don't wear women's clothes, I wear MY clothes !

  19. #19
    Senior Member JocelynJames's Avatar
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    A few months ago my wife and I were looking for something to do . As we passed a David?s Bridal, I said we could go in and she could try on a few dresses a la ? renewing vows? . She said I should try them on instead. She?s accepting of Joss, I have no idea why o didn?t .
    If you only knew the power of the pink fog! ~Joss

  20. #20
    I accept myself as is Gillian Gigs's Avatar
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    I had so many opportunities as a child, it makes me wonder what my mother was really thinking. There were several Halloween's where she encouraged me to let her dress me as a girl. More than once going out to the lake visiting family friends and being offered a girls bathing suit,(60's one piece) so I could go into the water. After marrying there were many times that the laundry bin was full, and I was offered everything from my wife's underwear, to a nightie. Then there was also the time it was very cold and I was offered a pair of pantyhose to help keep my legs warm. I chickened out every time, it makes me wonder if a had said yes.
    I like myself, regardless of the packaging that I may come in! It's what is on the inside of the package that counts!

  21. #21
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    I purchased some dresses from a charity/thrift shop a few years ago . The lady in the shop must have realised they were for me . She advised me I could try them on at home and bring them back if they didn?t fit . I felt embarrassed and never went back . The dresses did fit but I still should have went back . She could have been a good contact and become a friend.

  22. #22
    Member Christina89's Avatar
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    I wish when my father and his ex wife were still together that I told her about my crossdressing. She was always a kind hearted person. And never looked at a person for who they were on the outside, but who they were on the inside. And I regret not telling her about Christina. I feel she could have been a bigger help in Christina coming out a little earlier in life.

  23. #23
    Girl Power! CrossKimmy's Avatar
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    I once bought some shoes at a shoe store and was showing a friend my new purchase with my cute outfit on a crossdressing chat. She told me go back and show the SA my outfit with the shoes and to report back to her. I got a purse and sunglasses and my car keys. I must have closed the front door like 20 times but I ultimately chickened out. I would do anything to get this one back.

  24. #24
    Aspiring Member Brenda Freeman's Avatar
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    Like a few others here, my mom wanted to dress me up as a girl one year when I couldn't decide on a costume. I asked several questions, like what would I do for hair and others. She was very interested in doing this but I ultimately declined out of fear and regretted it. I know she wanted me to be a girl, she often would say with my curly hair I would have been pretty as a girl. I always wondered what she would have picked out for me to wear. I had tried on her girdles and nylons and slips. I will never know now. I think it might have opened up more opportunities and maybe discussions.

  25. #25
    Junior Member julia.bowie's Avatar
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    I saw another thread about if you could go back 20 years, what would you differently. And this one asking about missed opportunities. I tend not to look back or into the future - and believe in the new thing of the moment of "living in the now". The past is gone and the future is unknown - live for now.

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