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Thread: Regrets?

  1. #1
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    Regrets?

    In college, I was living alone, dating a bisexual girl who went as a "transvestite" for Halloween. She wanted me to wear the same outfit as her, and I refused, even though I really wanted to. I feel like I missed a huge opportunity to come out. I was too cool at the time, refused to give into who I am. Anyone else have times they could've made leaps and didn't?

  2. #2
    Aspiring Member MonicaPVD's Avatar
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    Regrets, I've had a few...
    But then again, too few to mention...
    I did what I had to do...
    I saw it through, without exemption.

  3. #3
    Miss Conception Karren Hutton's Avatar
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    I wish I had kept a date with a local girl in college.... would have learned how to polka! I regret not taking my mother up on her offer to dress me up as a girl for Halloween when i was like 8...

    I also regret that our High School Letterman Society, the year before i was eligible (9th grade)... dropped the hazing ritual where you had to dress up like a girl for a day a during school. That last year they did it (I was in 8th) one of the smaller guys got dressed by his mother and sister and you would have sworn her was born a girl. So cute! Come to think about it, looking back.. I's say that he had crossdressed before. just looked way to comfortable! But I missed out on that!!!

    Ohhhh and I regret not grabbing my grandmother's awesome girdle collection when she passed away. Think my mother and sister threw them out or gave them to goodwill. Many fond memories of those girdles.... when grandma was at work, and I was supposed to be painting her house... or weeding the garden! lol


    probably a few dozen more regrets....
    Last edited by Karren Hutton; 01-03-2021 at 11:37 PM.
    I reject your reality and substitute my own!:

  4. #4
    Silver Member JenniferR771's Avatar
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    Oh! Me too, my mother offered to dress me up as a girl for Halloween at my school for the day. I refused partly fearing the kids at school would have teased me.
    And my mother might discover how much I liked it.
    And then in college, my roommate may have figured it out when we shared an apartment.

  5. #5
    Gold Member Lana Mae's Avatar
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    I regret being naive about all this! If I had understood at a younger age, it might have been different, but...then what about my wife and two children? I guess it was better the way it happened!!! OK, no regrets! Hugs Lana Mae
    Life is worth living!
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    Monica is a frank Sinatra fan

  7. #7
    Aspiring Member kayegirl's Avatar
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    Not sure if it's a regret as much as I wonder what if.
    In my teenage years I had a girlfriend who was, shall we say, a bit of a tomboy. In the 2 years of our relationship, I never once saw her wearing a dress or skirt, although more than once she suggested that I might like to. And yes more than once I did take up her offer. We first met at a climbing club, and even after we had split up, continued to see each other at the club . The thing was that she became increasingly masculine in both appearance and mannerisms,. I lost all contact wits her and the club when I moved away for work, but I do often wonder how things would have been had we stayed together. I should emphasis that I am not unhappy with how my life has panned out since, nor do I particularly regret our parting company, but as I said at the beginning, I do wonder water if.

  8. #8
    Aspiring Member SaraLin's Avatar
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    H-m-m-mm. Here's one, but I'm not so sure it's as much of a regret as it is a "what if"

    At one point I became close with a lesbian friend, and she knew about my dressing desires - but I never found the opportunity to get my girl on with her around (lots of complicated reasons).
    I do sometimes wonder how she would have felt and if she would have dated me - as Sara.
    She's long gone (out of state). I've moved on and am happily married now. But every now and then I still wonder if anything could have come of it.

  9. #9
    Senior Member Angela1954's Avatar
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    No. No regrets really. I grew up in the 60's when dressing, transgender (if it was even called that) was so out of not only the mainstream but everyday conversation. I married, have two beautiful children, grandchildren, and a wife (second one who is open minded about my dressing). We never know what life would have been like if circumstances were different. If you are a good person, father, husband, grandfather, etc. the positives immensely outweigh any regrets.

  10. #10
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    Laurie,
    I guess you could ask do you know anyone who doesn't have regrets ? It's what makes life interesting and frustrating at times .

  11. #11
    Junior Member Amelia_Rose's Avatar
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    My biggest regret is that I did not come out to my wife earlier in our relationship. I've felt more shame over the secret keeping than the secret itself. We've had a long talk about it and she says she forgives me (for not telling her sooner), but finding that forgiveness in myself will take time I guess. I cannot ask for a more loving and supportive partner in life, and the fact that I did not tell her sooner feels like a betrayal of trust and a slap in the face for someone I trust and value so completely.
    Never forget that life is short. Whatever you believe, there's no guarantee of tomorrow or a second chance, so live your life the way you want! Be kind to yourself, be kind to others, and let's make this world a little brighter together!

  12. #12
    Reality Check Krisi's Avatar
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    I'm sure everyone has regrets, but if we had done the things we regret, our lives might have changed and we might not have the people and things in our lives that we have today.

    I switched careers on a whim; I saw an ad in the newspaper (remember those), interviewed and got the job. I met a guy at my new job, started playing music with his band on weekends and met my wife at a place we were playing.

    I suppose that's the opposite of "regret", but it's an example of how life changing a simple decision can be.
    Krisi

  13. #13
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    A few decades ago I was friends with a female coworker. I wanted more from the relationship, but she insisted on keeping it in the friend zone.
    In addition to the other attractions, we were of similar builds, so we could have shared a closet.
    Yes, I really thought of that.

  14. #14
    Miss Conception Karren Hutton's Avatar
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    Quote Originally Posted by BobbiKay View Post
    we were of similar builds, so we could have shared a closet.
    Yes, I really thought of that.
    I am guilty of choosing girlfriends in high school and college who were the same size as me so I could borrow their clothes!!

  15. #15
    Member Jemima Stephens's Avatar
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    I had a Girlfriend who would dress me up and we went for a walk around her village a couple of times which I found exhilerating. She then tried to persuade me to go to the pub in the next town to meet her friends whilst dressed, but I bottled it, both from a being found out by family point of view, but also I was in the Air Force at the time and that would have been construed as Homosexual behaviour which was against the rules at the time.

    I do wonder what would have happened if I had taken that extra step 33 years ago!

  16. #16
    Junior Member Deborah G's Avatar
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    Some years back, I had a long term girlfriend who I am 1000% positive would have no issue with my dressing. In fact, when we were on a trip to Niagara Falls, and I had forgot my underwear, she offered me her panties to wear! Later, on another occasion, she offered to apply make-up on me and then we could go out as girlfriends. Since we were about the same size, she said I could borrow her clothes, and she did not hesitate to try on some of mine now and then. Sigh, I would have none of it as I wanted to be the "macho man". After about a year, she lost interest in me and moved on, despite my attempts to rekindle any flame. Thinking back now, the last 30 years may have been completely different for me if I said "OK" to anything she proposed. Where is the "Way-Back" machine when you need it?

  17. #17
    Aspiring Member josie_S's Avatar
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    At least two ex-gfs asked me if they could put mascara on my lashes (i'm lucky that my lashes are full and long) and paint my toenails. Like Deborah, I was too caught up in being macho and pretended like that was the last thing I could ever want...sigh!

    Another involves a very good looking French man that was hitting on me at a bar on one of my early outings. I was so nervous and felt so self-conscious that I figured there was no way he was interested in me. I also think--despite the heels, french tip manicure, hoop earrings, cleavage, perfume, make up and LBD--that I was also still hoping, praying, that I could be the macho man LOL

  18. #18
    Senior Member NancySue's Avatar
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    Of course, but, I too, did it My Way.

  19. #19
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    The wife and I divorced for a 3 year period and then married each other again. In that 3 year gap we both had relationships with other people. I've shared this story with you before. The girl I was living with during that gap in the marriage actually got turned on by my dressing. Nothing was too much for her. If I got dressed up (MIAD), within about 30 minutes she would grab me by the hand and lead me into the bedroom for you know what. My wardrobe at the time was limited and she would share her clothes with me including making suggestions like which of her blouses would go with my skirt. I also caught her wearing a pair of my panties one time, hmmm?. We split up for other reasons (certainly not my dressing). My imagination runs wild thinking about what it might look like if I had stayed with her. She would have supported pretty much anything I wanted and would have likely initiated things I hadn't even thought of.
    Why fit in when you were born to stand out? - Dr. Suess

  20. #20
    Silver Member SherriePall's Avatar
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    I don't think I have any regrets. At least not along the line of dressing. I do have a few "phew, that was close" situations where if I had done this or that, I would immediately have regretted doing so.
    Sherrie Lynn Pall

    Sometimes I make sense and that frightens me.

    Please don't let me be the last post on this thread

  21. #21
    Member Christina89's Avatar
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    My 2 biggest regrets were not being honest with my mother when she first caught me with a stash of some of her clothes. And my second was not telling my stepmother. Her and I had a bond that was similar to that which my mother and I had. I feel that if I told both of them then I could have been a little more open when who I am.

  22. #22
    New Member Sunny_with_a_chance's Avatar
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    I'd say my biggest regret is not exploring this side of myself earlier. I grew up in a really normative male culture with an emphasis on sports and typical masculine bravado stuff.

    I'd always wanted to dress, try makeup, even do things like the school play, but shied away from it all because it wasn't 'normal'.

    While I am sad I didn't follow my heart earlier, I am glad to be who I am now. I think I did what I had to back then to thrive in that environment. Maybe I would've been happier, but maybe I wouldn't have too. Who's to say!

  23. #23
    best of both c2candice's Avatar
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    Two regrets that are related:

    1. I didn’t have the courage at a young age to explore this side of myself when I was single, and had more of an androgynous figure.

    2. I didn’t reveal this to my current wife right away in our relationship.

  24. #24
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    Hi Laurie , I regret waiting 72 years to get my ears pierced, All those years of clip-ons,

    >>>>>Orchid**OO**
    Having my ears triple pierced is AWESOME, ~~......

    I can explain it to you, But I can't comprehend it for you !

    If at first you don't succeed, Then Skydiving isn't for you.

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  25. #25
    Member Tabitha_Lynn's Avatar
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    Like Christina, I wish I had been honest with my mother when I was caught as a teen rather than pushing further into the closet.

    I love my life, today and wouldn't want to give up my family, but often wonder what it would be like if I had been honest with myself and others way back then.

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