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Thread: what are some missed opportunities you wish you made

  1. #1
    Member Christina89's Avatar
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    what are some missed opportunities you wish you made

    i saw someone on here post about a missed opportunity they had when they were younger. but i was wondering what are some of the opportunities you could have made yourself either younger or now that you would change. for me it would have been to be honest with my mother when she first found out about the stash of womens clothing i had hiding when i first started. or evening telling my old step mother about me dressing. her and i had a wicked close relationship. a closer one that i had with any of my fathers previous gfs. and she was always understanding about everything. i wonder what her reaction would have been had she known. and if she would have helped me out when they were together.
    I'm just a simple someone trying to figure life out.

  2. #2
    Gold Member Maria in heels's Avatar
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    Hi Christina!
    I think that we have all had your situation with someone else, I know that everyone in my immediate family knew about my dressing after I was "caught" by my stepmother. I talked with her so many years later (my father divorced her) which was very scary, even though she knew. I started to explain why, and we just didn't talk too much. My 3 sisters know from back then, and none made any comments. I recently discussed through texting with one of my younger sisters to explain why I think that Maria came about...

    Missed opportunities? I think that when I was younger, I had the chance to go out, but grew up before the internet. Girls today are so lucky, as it was very hard to even find someone, unless you looked at the classified in several of the "different" newspapers and maybe you could find someone to talk to. I only came out to the world in Januar 2019, attended some fabulous parties held by a local meetup group, and after going for several months, life got in the way and I missed so many months. I only wish I had started earlier, but I think that I'm still ok and not ready to go running down the street in my heels all the time...

    hugs
    Maria

  3. #3
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    Another opportunity I did not take advantage of was with the girl I dated after the girl I dated in HS. She was the 1st person I let know that I liked to wear pantyhose and she had no problem with me doing so. We wore pantyhose together a few times and she gave me a pair of brand new pantyhose to wear just because she knew I liked wearing them. Her brother used to have a costume party for Halloween every year and looking back on it I probably could have gotten her to help me dress at a lady for the party, but I never did so. Oh well! LOL

    Andy

  4. #4
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    I had a GF in college that claimed she had cross dressing parties in High School.
    I was an out of state student so couldn?t confirm her parties.
    She gave me a pair of thigh highs to put on and I got one up to my calf and quit. If I had heels I might have continued. If I had heels I might have quit without a dress, wig, bra, or dress. It?s hard to say.
    If things went bad between us, she could have held it over my head and exposed me. In retrospect, I wouldn?t have wanted to spend of the rest of my life with her.
    I?m better off with a DADT than somebody I could have opened up to at a younger age. Our current status is that I don?t believe my SO would let the cat out of the bag. We don?t want our child to know.
    I kind of like the secret, but am willing to open up more .

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    While away at college, I seriously considered transitioning but was afraid to lose my ultra conservative family. Back then being trans wasn't hip as it is among younger folks today. Most transwomen I knew of at the time were hairdressers, sex workers or freak entertainers (or any combination of the above). I made a reasonable decision, stuck with my male identity and have had a successful life. Not too long ago, I came across a transwoman I ran with during my younger years (we were both wild gender benders at the time) and let's just say that she has had a rough life. Who knows. I often wonder what could have been.
    Last edited by MonicaPVD; 04-02-2020 at 08:34 PM.

  6. #6
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    When I was 11 my girlfriend at the time wanted to dress me up in her clothes but I turned it down

  7. #7
    Junior Member Nicole Bernard's Avatar
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    I went on a solo cruise back in 1997.

    I decided to get a pedicure. My first ever.

    I really wanted to get my toenails painted but was very nervous about it.

    It was a young man doing the pedicure.

    He was done and looked at me with a knowing glance and asked it there was anything else I wanted.

    I chickened out and said no.

    I wish I would've said that I wanted them painted.

  8. #8
    Senior Member Angela Marie's Avatar
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    Probably trying to kid myself that my dressing was just for fun; rather than admitting my true feminine feelings. Only last year did I finally come to grips with this.

  9. #9
    Silver Member NancySue's Avatar
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    I met my to be fianc? in college. She figured out my attraction to hose. Even though they weren?t her favorite article of clothing, she?d wear them for me. On one of our dates, she brought a pair of pantyhose and asked me to wear them. She even offered to help me put them on. Stupidly, I declined, but she knew. Sometime later, she offered again. This time I said OK. It was fantastic. She brought me a pair of her panties, but they didn?t fit, so she bought me a pair my size. She wanted to go farther, but I got chicken. Looking back...a missed opportunity.

  10. #10
    Exploring NEPA now Cheryl T's Avatar
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    I was about 10 or 11 and at my aunt's.
    She went out for something and I was in her bedroom trying her shoes on when she returned and caught me. She didn't get mad but did tell me if I wanted to wear her things that I should just tell her and she would help me. Of course I was too scared for that and never requested her help.
    I always wondered how my life might have gone had I accepted her help.
    I don't wear women's clothes, I wear MY clothes !

  11. #11
    Member Lux's Avatar
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    During college I dressed whenever the opportunity came up. I would go to dance clubs in the nearby city and have a great time. Back then, I would even sometimes attend a large lecture dressed up and sit in the back wearing cute clothing.

    One time I went to an on campus clothing consignment store in male mode and was the only customer in the store. I was looking at these amazing pair of 5” black stiletto heels and the female employee came over and asked me if I wanted to try them on. Being naturally shy at that age, I was a little taken aback. I think if she had asked a few other questions first I may have responded differently but unfortunately I kinda froze and changed the topic. We talked a lot and I realized she was definitely flirting with me. She was naturally so beautiful and I think nerves overwhelmed me and I sort of ran out of there.

    Always wondered what would have happened if I played it cool and just asked her out. College is such a great time for experimentation.

  12. #12
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    The only thing that I wonder about is a girlfriend told me about her dad finding her mother's night gown and asked if I knew what he did? I think that he may have been a crossdresser. I didn't have the nerve to guess he was a CD.

    I've had a great life and changing it might not have been as good.

  13. #13
    New Member Janica's Avatar
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    When I was in my early 20's, the group I hung out with would meet to drink at a local bar on fridays and saturdays. One girl, a lady to me then, she was also in her 20's, had been manager of a local Woolworth's. She casually mentioned that she took their entire hosiery inventory when they closed. She was always in a skirt and hose and had fantastic legs. I had a huge pantyhose fetish but was so shy and insecure I didn't even know how to reply. I wish I had asked to see her collection. I think we could have made a great couple but I didn't even try to be with her. I think about that moment and her a lot still...30 years later...what could have been?
    Last edited by Janica; 04-05-2020 at 04:22 AM.
    The most terrifying thing is to accept oneself completely. ~ C.G. Jung

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    You certainly have the legs for that collection as well

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    Aspiring Member Karmen's Avatar
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    I wish I'd come out to my family and friends when I was still a kid. I was thinking about it back then, but didn't want to lose my conservative friends and have problems with family. Later on, it just seem even harder to do that. But as some of you pointed, who knows how would my life turned out if I done that with the society I live in.

  16. #16
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    i often think my late mother knew i had worn her girdles and nylons, she got a dress from a lady she worked with for me to wear on halloween but i chickened out

  17. #17
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    When I was a teenager and developing an interest in wearing my mother's clothing I am sure my parents, especially my mother, knew I was dabbling in her lingerie draw. Why else would there be a snapped strap on her only black bra? My parents tried to catch me several times. I escaped confirmation. If I had been caught I am sure my ass would have been whipped raw. That's not a figure of speech. My mother did a good job swinging a belt across my legs when I deserved some sort of discipline. The benefit of not getting caught was not being thrown out of the house after high school. I would have ended up in the army and go to Nam four years earlier. Nam in 1966-1968 was not a good place to be.

    Fast forward to marriage. My wife and I did incorporate nylon gowns and hosiery into bedroom play until it became evident my interests were more than a "kinky" bedroom "fetish" with benefits for both of us. She was turned off by my cross dressing; "If I wanted to be married to a woman I would have married a woman."

    Over the recent years, since our kids have been out of the house, there were probably missed opportunities to further discuss the "elephant in the room." One separate occasions she did find a bra and a panty that I failed to store away. Or unpopped water balloons in the kitchen sink. Or finding the browser open to this forum. She did not go ballistic. Or make snide comments. She just made a declarative statement she had found those garments and placed them on top of the dryer behind closed doors. Or I should be more careful when walking away from the computer in case a visitor came to our home.

    Perhaps I should have tried to open a conversation, but, I know two things. First, she does not appreciate my cross dressing. Secondly, she knows after almost fifty years I am still the man she married and wanted to marry. She has made the realization my interest has nothing to do with her femininity or sexuality. It is my thing. Full man plus a little more.

  18. #18
    Aspiring Member LIKETODRESS2's Avatar
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    My mom asked if I wanted to dress as a girl for holloween when was in 6 in grade I was to scared because I though the would find out how much I liked it, Fast forward 8 years was caught by her she freeked out. Wish I would have that day and been able to say You let me d it before so what the big deal

  19. #19
    Paula Paula_56's Avatar
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    I dated a woman, who came out to me as gay while we were dating. In my early 20's, 1980 I was afraid to tell her that I wanted to be a woman.

    We both were loved each other, yes loved two humans one gay one trans, we loved each other.

    I regret no being honest to this day.

    We all forget, gay people were being fired and harassed publicly without, as far as transgender the word didn't even exist.

  20. #20
    Silver Member Kay J's Avatar
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    I wish i would of talk with my mom now i know she knew but never said anything plus she found my stash and folded everything up real nice. If dad ever found out it would of been all over for good!

  21. #21
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    I wish I could've started crossdressing earlier in life. When I worked at the movie theatre and Sex and the city 2 came out, a lady from a women's clothing store was giving away coupons. I jokingly asked "where's mine?" and she offered me one, saying she gets "many of those people (crossdressers) in her store. I turned her down politely because I did not consider myself to be a crossdresser at that point in my life. Sure I wore a Princess Peach cosplay outfit every chance I got when I was alone, and I actually owned a couple of feminine clothing items, but I still cringed at the thought of wearing women's clothes because hey, I wasn't sick or anything!
    Soon after though, my curiosity got the best of me as I kept on thinking about what it was like to wear these types of clothes. I started going to Walmart late at night to get panties and a couple of other things. But I constantly wished I would have accepted that lady's offer.

  22. #22
    Aspiring Member StarrOfDelite's Avatar
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    Quote Originally Posted by Paula_56 View Post
    I dated a woman, who came out to me as gay while we were dating. In my early 20's, 1980 I was afraid to tell her that I wanted to be a woman.

    We both were loved each other, yes loved two humans one gay one trans, we loved each other.

    I regret no being honest to this day.

    We all forget, gay people were being fired and harassed publicly without, as far as transgender the word didn't even exist.
    I had a similar, but different, experience when I was in college. I was part of a group of 20-30 males and females who hung around together. drinking beer, going to ballgames and concerts, talking about life, love, sex, politics, and academics. There was a lot of dating inside the group, some of it serious, and some of it platonic. I dated one of the girls semi-seriously about a dozen times. We never had sex, or went much beyond a few kisses, and I didn't press her or vice-versa. About ten years after graduation I learned at a class reunion that she had come out as Lesbian and was the social leader of a group of high profile Gay women in a large midwestern city. At the time it was not much more than a surprising revelation which made me shake my head and smile a bit, since it took me 35 years plus to reach self-realization. After admitting to myself that I am transgender, I've often wondered if she and I sought each other out because we inchoately recognized that we were both "different." If we had been more open and honest about our personal feelings I'm not sure whether that would have affected the way I've lived my life. Given the societal opprobrium which was directed at anyone who had alternate lifestyles in that era undoubtedly I would have been shunned as a deviate by prospective employers in the conventional professional and corporate world.

  23. #23
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    A couple of occasions come to mind.
    I had a girlfriend who accepted my CDing as long as it wasn't all the time and restricted to indoors. She wasn't totally into it, but accepted it. We split for reasons that were nothing to do with CDing. I suspect if we'd stayed together, her acceptance might have grown stronger.

    The second time was when my first wife and I separated. She knew I wore panties and accepted it. When she moved out of the house, she left behind a lot of clothes that she had overlooked in one closet. They remained there for about 8 months and she never came back to collect them, so she clearly had forgotten that she even had them.
    I eventually took them to her house and gave them back.
    Most of her clothes were a perfect fit on me, so I could have kept them in my own collection.

  24. #24
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    I smile reading posts about how we are not sure if our mothers knew that we tried on their intimates. Lol. My mom knew. Your mom knew. When you take care to fold your intimates and place them in a dresser drawer, you know exactly how you folded and placed every. single. piece. Even the tiniest disruption stands out right away. Anyway, when I was a kid I thought I was outsmarting my mom. Silly rabbit!

  25. #25
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    A couple missed opportunities come to mind. I was working in a corporate job in my early 20's. There was a girl with whom I was friendly who on at least two occasions made suggestions about me crossdressing. It sort of came out of nowhere but she brought it up twice and she was not kidding around. We liked one another and I know she was interested in dating me. I did not even react when she brought up the crossdressing idea. I was scared of revealing myself and talked myself out of asking her out. Although I was scared of being revealed at work she would never have said anything. A year later she met a guy and got married. In retrospect, I realized I had been a complete idiot.
    Not that I learned because ten years later I blew another chance. I occasionally would put a personal adv in the paper (this is the 1980s) as a guy who crossdresses looking for a woman. It was rare to get a real response and generally when I did get one the person who responded did not sound like someone I wanted to know. In this case, I had just moved to California and got a response from a woman, around my age, who expressed real interest in getting together and exploring it together. She sounded like a real person who I may have liked. We corresponded quite a bit but, in the end, I managed to talk myself out of meeting her. There were some other things going on at the time which influenced my decision, but again, it was stupid. In truth, I was scared of my own needs and desires.
    Another 10 years passed before another opportunity arose from a personal adv but this time I did not blow it (finally). I've been happily married to that person (my wife) for almost 20 years.

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