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Thread: Missed Opportunities

  1. #1
    The non-Mint Starla Starla's Avatar
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    Missed Opportunities

    Growing up, was there ever an opportunity to dress as a girl for "legit" reasons, and you failed to take advantage of it? Maybe someone suggesting dressing like a girl for Halloween, or being asked to be a Powder Puff cheerleader, or even just goofing around with an older sister? A situation where you had a good "excuse" to crossdress, yet chickened out?
    "Television is very educational. Whenever somebody turns it on, I go into another room and read a book." -- Groucho Marx

  2. #2
    Miss Conception Karren H's Avatar
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    My mother offered to make me a dress for Halloween a number of times in grade school... During the "you were supposed to be a girl" period of my life. I was too embarrassed to take her up on it.. Like 8 or 9 years old.. And I'd been wearing her things for a few years by then... In high school they had a number of initiations. Where the guys had to dress as girls. But by the time I would have been eligible. They had dropped them all.. born too late. Lol.
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  3. #3
    Silver Member Debra Russell's Avatar
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    I remember in High School (I went to a private christian school) we had a hawaiin day we were all susposed to dress in island mode; a bunch us guys us were going to wear mumus I chickened out --they all got suspended becaused it wasen't appropriate attire for boys -- but I wanted to

  4. #4
    Member FionaO's Avatar
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    In my first year at college a guy on the same floor as me in the Halls of residence said he would pay for me and a date to go to the Hall Formal dance if I dressed as a girl but I chickened out. A few years later when I was married a young college student who was a family friend asked me to go to her brother's wedding dressed as a girl and pretend to be an ex girlfriend in order that she could play an elaborate joke on him. I agreed but two days before the wedding I took ill and ended up in hospital. It was the only time in my whole life that I have been in hospital.
    Strangely enough I have just posted on another thread that going to a formal dance and a wedding en femme are my two biggest fantasies. Funny how things work out.

  5. #5
    Member Misty G's Avatar
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    I think I took advantage of most oppertuneties can't remember missing any

  6. #6
    Aspiring Member Chiana's Avatar
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    This subject makes me feel a little sad. I always really liked my Mother's lifelong best friend, Esther. Looking back now, I am sure from a very early age that Esther had me figured out. While she did not come out and openly push for me to dress, there was always some subtle encouragement for me to play dress up. I remember at a very young age (maybe 4 or 5) she often talked to my Mom about letting my hair grow long. I thought it would be wonderful but Mom & Dad did not give in on that. It seems like every Halloween, she wanted me to dress as a girl. And there were many more clues that she understood my desire to dress, maybe more than I did. Beyond that, I really did feel close to Esther. She was sophistcated, intelligent, artistic and fun. One summer, when I was about 13, she convinced my parents that it would be really fun for me to go live with her for summer vacation. At this time, she lived about 150 miles away. My parents agreed. To this day, I can't explain why, but for some reason I decided to stay home that summer. Looking back, I think I probably missed a possible life changing summer experience. A few years after that, Esther died of complications from surgery. I don't know if there is any one thing I regret more in my life than missing that summer with Esther.
    Whether you think you can, or you think you can't, you're right.

  7. #7
    Wanna-Be Girl Jenna Lynne's Avatar
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    One year, our school play was "Charley's Aunt." I had been in several plays, and tried out ... for nothing in particular, just any part at all. The drama teacher posted the cast on the bulletin board, and guess who had been chosen to play the crossdresser! I thought I'd sink down into the floor and die right there, all the kids standing around and SEEING that the teacher had picked me out as a wanna-be girl.

    I went to the teacher and mumbled something about how I couldn't do it because the rehearsals would conflict with something else I was doing. I've always wondered how my life would have been different if I had done the part.

  8. #8
    Member paulaluvssz8's Avatar
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    When I was growing up there were many opportunities for me to be dressed by neighborhood friends.(GG's) That was a total "no no" in the 80's in the south. Like Karen, my mother always told me and one of my brothers that we "were suppose to be her girls". That she just cried when she had all boys.... I don't know if there were more times that I missed from her wanting to dress me up. But I'm confused about a lot of things anyway... LoL
    No, those are my Panties]

  9. #9
    The non-Mint Starla Starla's Avatar
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    Quote Originally Posted by Chiana View Post
    This subject makes me feel a little sad. I always really liked my Mother's lifelong best friend, Esther. Looking back now, I am sure from a very early age that Esther had me figured out. While she did not come out and openly push for me to dress, there was always some subtle encouragement for me to play dress up. I remember at a very young age (maybe 4 or 5) she often talked to my Mom about letting my hair grow long. I thought it would be wonderful but Mom & Dad did not give in on that. It seems like every Halloween, she wanted me to dress as a girl. And there were many more clues that she understood my desire to dress, maybe more than I did. Beyond that, I really did feel close to Esther. She was sophistcated, intelligent, artistic and fun. One summer, when I was about 13, she convinced my parents that it would be really fun for me to go live with her for summer vacation. At this time, she lived about 150 miles away. My parents agreed. To this day, I can't explain why, but for some reason I decided to stay home that summer. Looking back, I think I probably missed a possible life changing summer experience. A few years after that, Esther died of complications from surgery. I don't know if there is any one thing I regret more in my life than missing that summer with Esther.
    Wow, that's really a bittersweet story, hon.

    It exemplifies something that I've noted in reading many "life stories" of TG folk. It seems like often it is not the mother who kind of senses those things, but someone more distantly related, or even unrelated. An aunt, a cousin, a grandmother, a family friend. It's almost like they are more objective -- like the Mother is ironically too close to the situation to see the forest for the trees, and too invested in raising a "normal" child to grasp the meaning of the little signs that she may even notice, but subconsciously dismiss or ignore.
    "Television is very educational. Whenever somebody turns it on, I go into another room and read a book." -- Groucho Marx

  10. #10
    Member Davina-Alba's Avatar
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    No, I took every available opportunity and even suggested a few.
    I am a man and I just want the freedom to wear what I want in public or private. Is that really too much to ask?

  11. #11
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    I never had an opportunity for cross dressing proper.. There was a year when the guys had to wear tights for the annual Christmas show but my mom would "never force a son of mine to wear tights"..

  12. #12
    Platinum Member Angie G's Avatar
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    Never happened wish it had.
    Angie

  13. #13
    happy to be her Sarah Doepner's Avatar
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    I've been trying to think of an opportunity that someone else offered and couldn't come up with a single one. Drat! It would have been fun if just once I'd been able to dress en femme without planning my escape and/or excuse if anyone saw me.
    Sarah
    Being transgender isn't a lifestyle choice. How you deal with it is.

  14. #14
    Woman and loving it LitaKelley's Avatar
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    My mother was dating the VP of a motorcycle club.. he was a mean, rough and tough sonofabitch.. He lived with us for several years.. at the time, I was continually getting into fights in school because I had long blonde hair and wasn't as masculine as the other boys.. This was 7th or 8th grade I think.. So.. one day I come home with a black eye... and he gets MAD and tells me that if I don't fight back and kick their asses that he'll make me go to school in a pink dress.. He told me to go to the biggest kid in school and give him an ass whooping or he'll make sure I wear a dress every day until I do... Anyway, I did exactly what he said and none of those kids ever F'd with me ever again.


    When I was around 14 or 15, my sister and her best friend pestered me a few times to allow them to dress me up and put makeup on me.. I refused.. Little did my sister know that I've been wearing her things for years.... I always hoped for and wanted my sister to ask this of me when alone, because it's her friend that's the reason I refused, because I had a mad crush on her.

    During high school, the majority of my friends were girls.. I spent alot of time at girls' homes, going to malls, etc.. this was platonic friendships, not like BF/GF... anyway, one of them wanted to dress me up and I said no.

    The summer after graduation, I hung around with several friends whom were into the "Rocky Horror Show" and attended regularly to this at the theater where people performed in front of the screen, etc... More than several times I was asked if I wanted to dress in "transvestite" and repeatedly told that I would make a "great girl".. yet I refused.

  15. #15
    Member Davina-Alba's Avatar
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    Quote Originally Posted by LitaKelley View Post
    My mother was dating the VP of a motorcycle club.. he was a mean, rough and tough sonofabitch.. He lived with us for several years.. at the time, I was continually getting into fights in school because I had long blonde hair and wasn't as masculine as the other boys.. This was 7th or 8th grade I think.. So.. one day I come home with a black eye... and he gets MAD and tells me that if I don't fight back and kick their asses that he'll make me go to school in a pink dress.. He told me to go to the biggest kid in school and give him an ass whooping or he'll make sure I wear a dress every day until I do... Anyway, I did exactly what he said and none of those kids ever F'd with me ever again.


    When I was around 14 or 15, my sister and her best friend pestered me a few times to allow them to dress me up and put makeup on me.. I refused.. Little did my sister know that I've been wearing her things for years.... I always hoped for and wanted my sister to ask this of me when alone, because it's her friend that's the reason I refused, because I had a mad crush on her.

    During high school, the majority of my friends were girls.. I spent alot of time at girls' homes, going to malls, etc.. this was platonic friendships, not like BF/GF... anyway, one of them wanted to dress me up and I said no.

    The summer after graduation, I hung around with several friends whom were into the "Rocky Horror Show" and attended regularly to this at the theater where people performed in front of the screen, etc... More than several times I was asked if I wanted to dress in "transvestite" and repeatedly told that I would make a "great girl".. yet I refused.
    Hmmm. You really have missed some golden opportunities.
    I am a man and I just want the freedom to wear what I want in public or private. Is that really too much to ask?

  16. #16
    Silver Member noeleena's Avatar
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    Hi.

    Will this count tho not a missed one,

    !958 age 11 -12 dressed as a girl in front of 80 to 100 people & my Mum , dress , top , make up the whole works , doing a mime for our church end of year break up 5 of us lads & 4 of us dressed, as girls. we mimed a song. i think we sang it as well, the song was about we are sitting in the back seat having fun while you the boy keep your hands on the wheel.& your eyes on the road ahead.
    & it went over well. sorry no pics & i went home still with make up on.

    ...noeleena...

  17. #17
    Silver Member linda allen's Avatar
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    I've had a few opportunities to dress as a female for halloween and I've done it, but not very well. Pretty much a dress and a bra stuffed with socks (doesn't look right or feel right). No wig, no fanny or hip padding, no heels, no makeup, etc.

    So, my regret is that I didn't take it further when I had the chance. Of course, if you do too good a job, people will wonder .......
    [SIGPIC]http://www.crossdressers.com/forums/image.php?type=sigpic&userid=82706&dateline=137762 0356[/SIGPIC]Linda

  18. #18
    Gender adventurer JamieG's Avatar
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    Quote Originally Posted by Carly D View Post
    I never had an opportunity for cross dressing proper.. There was a year when the guys had to wear tights for the annual Christmas show but my mom would "never force a son of mine to wear tights"..
    This reminds me of when I was taking a Theater Arts class in high school. We were doing a medieval-fantasy play, and the teacher told us that we should get tights and tunics for our costume. I told my mom, trying to sound as reluctant as possible, "Mom, the teacher says I need to get tights for my costume." She just goes, "Don't worry about that. We'll just get you some pants instead." I think I hid my disappointment really well. I have to wonder if she would have gotten them for me if I had sounded like I was okay with the idea.

  19. #19
    Gold Member JenniferR771's Avatar
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    Yes! Actually my mom wanted to dress me as a girl a few times for Halloween. I declined. Afraid I wouldn't look good. Or that I would look too good. Or that I would reveal my secret. Or be teased or hit on by the more masculine and bigger boys. One of the other classmates dressed as a woman--looked really good--sigh--I wished I had done it, too.
    And 10 years later my best friend's girlfriend told me how they dressed up a friend for ladies night at the theatre (half price for girls). Two months later I said I thought I would like to try it. She had no dresses on campus, she said. Later she gave me a gift--one of her old bras, as a going away present when I transferred schools. Not sure, but I think as a couple they suspected the truth. They wanted me to try it on; I refused. Sigh.
    Last edited by JenniferR771; 12-18-2010 at 10:40 AM. Reason: spelin

  20. #20
    Aspiring Member DebsUK's Avatar
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    When I was maybe 14 or 15 I went to a youth club and we were doing a float at the local gala. The theme was to be movies, so there were lots of characters from various films including St Trinians girls who were all guys from the club. I ended up being a cameraman, but if I'd had the guts I'd have loved to be one of the schoolgirls.
    I also grew up around the time of the New Romantics. I rue the time I was more interested in rock music and joining my own "tribe" of rockers when I'd so much rather have been wearing makeup and girls clothes while listening to Duran Duran

  21. #21
    Member Davina-Alba's Avatar
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    Quote Originally Posted by DebsUK View Post
    ... there were lots of characters from various films including St Trinians girls who were all guys from the club.
    Ronald Searle who founded St Trinian's has a lot to answer for. The first time I experienced the sexual pleasure of cross dressing was dressed as a St Trinian's 6th former (I was 9 or 10). Apart from that dressing as a St Trinians Girl has given thousands of men the excuse to get into stockings, suspenders, knickers and bras without anyone questioning their motive. A couple of years ago I took part in a St Trinians charity pancake race.

    Lets hear it for "St Ronald" patron saint of cross dressers.
    I am a man and I just want the freedom to wear what I want in public or private. Is that really too much to ask?

  22. #22
    Adventuress Kate Simmons's Avatar
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    A "miss" is as good as a mile Starla. in this or any other "game".
    Second star to the right and straight on till morning

  23. #23
    Silver Member linnea's Avatar
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    I had a few opportunities, but there were too many social/cultural reasons why I could not take advantage of them. I've often thought that I might get an opportunity in theater where I've been pretty active, but nothing ever panned out.
    Now, I'm slowly working on a female role in a one-act play, but I don't know where or when I will be able to produce it--time will tell on that.
    Like some others, I was born too early!
    warmly, Linnea

  24. #24
    Call me Celes!!! the_me's Avatar
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    In summer there was a run for breast cancer where all the men have to dress in drag, I regret missing out on that. Seeing pics of some trying to jog in heels was pretty cute/funny though!

    Also Halloween, of course. Should have, but already had the Star Trek medical outfit planned with a friend and went as Julian Bashir from DS9 instead. Next year for sure though, I hope to have a nice kimono (or at least a cute yukata) by then, so maybe will go as a geisha.
    With love,
    - Celes

  25. #25
    Silver Member Amy Hepker's Avatar
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    I did get dressed up by my sisters when I was young and I remember that I liked it, maybe to much. It never happened again, my dad would have gotten really mad if had found out I enjoyed it. One time I remember when I did get dressed up I was the one who mentioned it to me Girlfriend and she said OK and dressed me in a Bra, Panties and a Purple dress that zipped up th4e back. I was in seventh heaven, I was at her mothers house and she made me show her mother. Then her brother came home and she wanted me to show him but I ran upstairs and tried to take it all off before he seen me, but I had a hard time getting the zipper down and he pushed thru the door to see me in Bra and Panties. I then decided I might as well get dressed back up again and with the help of my girlfriend I did. She later walked around the block with me dressed like that, but I had to instagate that also.
    Ladies have a GREAT time!
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