Missed Opportunities

[Starla]

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?

[Karren H]

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.

[Debra Russell]

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:o

[FionaO]

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.

[Misty G]

I think I took advantage of most oppertuneties can't remember missing any

[Chiana]

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.

[Jenna Lynne]

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.

[paulaluvssz8]

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

[Starla]

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.

[Davina-Alba]

No, I took every available opportunity and even suggested a few.

[Carly D]

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"..

[Angie G]

Never happened wish it had.:hugs:
Angie

[Sarah Doepner]

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.

[LitaKelley]

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.

[Davina-Alba]

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.

[noeleena]

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...

[linda allen]

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 ....... :heehee:

[JamieG]

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.

[JenniferR771]

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.

[DebsUK]

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

[Davina-Alba]

... 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.

[Kate Simmons]

A "miss" is as good as a mile Starla. in this or any other "game".:)

[linnea]

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!

[the_me]

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.

[Amy Hepker]

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.

[Debglam]

In first grade (early 1970's) we had some kind of May day/field day type of thing and they were going to have a touch football game and the other boys, myself included, were going to dress as cheerleaders. I was thrilled. The teacher sent home a note to that effect and how we should dress. My mother, and a couple of others if I recall, had a fit about this - boys dressing up as girls. This aspect of the event was cancelled. Is it any wonder I'm now dealing with this in my 40's? :sad:

[Shelby]

Back when I was in High School, we had opposite sex day for one of the dress-up days. I started asking a few of my cheerleader friends about borrowing their uniform for the day. My one friend that I asked was smaller then me but she was such a hottie and would eventually become the Homecoming Queen the following year. Well she that I wouldn't fit in her uniform. I remember her putting her hands on either side of my waist to get an idea of size and confirmed that I would be able to fit into her uniform. However, she invited me back to her house after our theater rehearsal to see if there were anything else in her closet that would fit me. At the time I was relying on a ride home and would have had to call my parents to come into town and pick me up at a girls house. What would I have said to my mom? That I was at Candy's house studying? Like she would believe that, so I turned her offer down and just went home. The dress-up day was a total bust anyways. But I still regret not taking her up on her offer and going through her closet trying on her clothes.

[Rachel Morley]

I have one regret in this regard. When I was 19 my 17 year old girlfriend Mandy (who was an apprentice hairdresser) and her best friend Tina wanted to give me a makeover. I remember this so well. We were in the kitchen of her parents' house on a Saturday afternoon. I had quite long hair back in those days and they wanted to wash and style it with rollers and curls etc, then put full makeup on me and also paint my finger and toe nails. They didn't mention dressing me up in their clothes (although that might have ended up happening too) what they wanted to do was the hair, makeup and nail polish. I said no as I was too chicken to do it as her Mom was in the house and I didn't know if her Dad would come back from wherever he was. I was too scared to be seen having this done to me. :o Looking back on it now ... I realize I was such an idiot! :sad:

[Raychel]

I was probably only 12 or 13 years old, I was over one of my friends house, His mom was smokin hot along wit 2 smokin hot sisters. Way closer to my age then the mom. Well the sisters decided it would be fun to give me a complete girly makeover, all dressed up and complete makeup.

I was way too young to even think about how much fun it could have been. I just chickened out and went home.:doh::doh:

I would bet that if a similar situation were to arise now. Things would definitly play out different. :daydreaming::daydreaming:

[Frédérique]

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?

No, it was all clandestine, and that’s how I like it. There was NO opportunity to crossdress when I was growing up. I have two sisters who are much older than me, so their clothes wouldn’t fit, nor was I allowed in their rooms for any reason – I would’ve been punished, no doubt about it. There were no aunts, babysitters, or other sympathetic feminine mentors in my childhood world, and I was expected to be a boy, period – there was no room for experimentation at all, until I isolated myself from those around me. I was strictly a boy in male costume on Halloween, and “dressing up” as a girl was not even an idea, or a dream worthy of contemplation. In my world, growing up, the genders were miles apart and expected to remain so. Looking back, I wish I had the opportunity to crossdress, but it never would have been “legit” under any circumstances. There are other things I wish I had tried when I was young, but this is not the time and place for that off-topic discussion…
:naughty

[Loveday]

Well I think I may of mentioned this before in another thread. My x wanted me to dress to go shopping with her. I didn't do it because I thought I was being set up for the divorce, especially when she started talking about pictures. So if I had, I probably would of started doing this long ago...it's fun.