Do you have Vivid Memories of the first times you saw Men Dressed in Women's things

In both real life and in Media ?

For those of us who are older, and before the internet there were few and far oppurtunties to see guys dressed as women so at least for me everyone of them sticks in my mind. I will only mention a few and hope you will share yours . Do others have strong memories like mine.

The one thing that never changed was that all the situations were comical and the women I was with found it way more amusing than the men.

The First was going to see the Vienna Boys choir with my family. After several fun skits almost half the boys came out in pretty peasent dresses, petticoats and wigs and proceeeded to sing and dance around like silly girls ! the audience loved it and it was my sisters favorite part of the show. I was jealous of how cute the boys were in their dresses.


The second was attending a popular TV game show in LA called " Truth or Consequences " in person with my family and crazy Aunt Ann.

Anyway everytime the show started on TV when they panned the audience they were all laughing Histerically espcially the women. But they would never show what they did to get the audience so worked up.
When the curtins opened two men from the studio audience were on the stage in robes accompanied by the pretty display models (picture Vanna White), with suitcases in front of them. The audience was told that the fastest one to get dressed would get $100 and the other $50 When the horn was blown the men took off their robes to reveal they were in white briefs that looked more feminine than masculine. When the suitcases were oped by the models it became clear to everyone that they were filled with beautiful Feminine clothing. Starting from the top with the minimal help and guidence from the models the men raced to put on Lacy Stuffed Bras, squeezed into Panty Girdles ( my mom's girlfriend Ann's favorite part) put on stockings and attached them to the garters, stepped into a beautiful silky & lacy Full Slip, put on heels, stepped into and were zipped into a feminine dress, put on a Jackie O type hat and had to grab a purse and walk to the other end of the stage. Ann said it took all of about 4 minutes but was the funniest thing her and her girlfriend had ever seen, she said it was so fun to see men have to put on and wear women's things! My sisters and mom thought it was terribly funny and loved the story, my dad and I were not as convinced. Our reaction was noted by mom and for several minutes the ladies attempted to get us to try the "The Suitcase Race" But my dad would not go for it. So everytime I watched the show I wondered if they used that skit ever again ?

It probably happened earlier but as a kid in the early 70s I used to watch the Danny LaRue show. Danny was a drag act and was hugely popular with not only his own series but appearances on many others. I was about 6-7 and was fascinated about how this man could look so much like a girl, especially when wearing a tutu or showgirl type outfit. Later in the 70s seeing men dressed as women became more widespread in films and plays. Not sure how much influence it had on me but it sticks in my mind.

I don' have any specific memory but do recall some shows where silliness was the goal. I don't recall ever seeing anyone as a crossdresser besides myself in the mirror. The internet has made all the difference in all of our lives for being and understanding ourselves. The show you talked about sounds hilarious! I'm going to google it as soon as I'm through here....who knows....maybe it would be a good thing for an organization to do to raise money!?!!

In the media, well Danny La Rue, who my Mother thought was marvelous, then Leslie Dawson, who my Mother hated! Can't say why she felt that way.
In real life, apart from myself, I think that the first time that I was aware of it, it would have been my first wife's father, at some party or other.
None of these were influences on my own cding, although I do believe that the Father in law did make it easier for myou first wife to accept my dressing.

I was in San Francisco for company training Halloween of 1977. I do not recall any parade. Maybe there was none in 1977. However, after work the spectacles on Gearly Blvd were quite amazing. I did not think what I was seeing had anything to do with what I personally envisioned cross dressing to be all about. Anyway, a group of us trainees were at a nice restaurant for lunch one day. I saw two attractive cross dressers or transwomen at the restaurant. Their presentation was excellent. The thing that drew my attention was their height, and, their throats...i.e., Adam's Apples.

I know I had seen and still see some movies or televisions shows with cross dressing. I am not entertained by any of the supposed comedy on these shows and will not watch them. I take wearing women's clothing to be a serious personality issue, and, nothing to be made light of.

OMG ! Danny La Rue ! I discovered him later ! I only wish I could look half as good as he did as a French Maid !Attachment 271209

First time I saw someone besides the drag queens in the clubs , I was driving in NYC to a club, we were in the meatpacking district, and spotted a dude in a dress a mile away on the sidewalk, the hunchbacked, bowl legged , fast paceed walk was a dead giveaway from far FAR away...its NYC this isnt a rare sighting...but it was just a hot mess.

Can't remember first time I actually saw a MtF CD live.

But do remember the movie "Some Like It Hot". My mother wasn't going to let me see that when it first came out 1959/60, the old deny what you don't want to happen offense. Saw it years later somehow.

Was able to find some stuff about Christine Jorgensen and also CD in larger libraries. Also found occasionally articles in the trashy magazines, and later when in NYC in the 42nd street district.

So I'm 42... I don't remember exactly, but I'm pretty sure it would either be:
Jack Tripper behaving badly,
Tom Hanks in Busom Buddies,
Monty Python?
Tootsie would have come later.

Those are all comically poor examples.. we could probably just as easily ask "when was the first time you saw a clown?" - or a cross dressing clown?

Ah...
That was Dumbo.. I guess that takes first.

There was an old man who came to my church when I was young. Everyone called him Screwy Louie. He wore a dress and high heels. He had some sort of head wound. Quiet guy.

Then there was Klinger from MASH.

Then there were others like Monty Python, Bosom Buddies and a recurring character on All in the Family.

Oh yeah!! Thanks for reminding me about mash! Forgot that one!!

I am not sure if this was my first but it was certainly the standout, I remember seeing a picture of Caroline Cossey in a newspaper I must have been around 16 or 17 years old at the time. I had CD but did not at that stage think anything much of it. I remember being fascinated by that picture and her story.

No not really

I was teenager when the movie Tootsie came out. And it wasn't till late in my 20s when I started crossdressing that I saw my first real life man dressed as woman.

Probably Benny Hill.

Hi Robbie:hugs:, I guess my earliest was Uncle Miltee om the Milton Berrile show back in the 50s'...:daydreaming:...

I was with my mom at a grocery store when i was a little boy, we saw a man in a dress. I did not really think much about it. He was dressed nice, that image stuck with me and within a year i was stealing my mom and sisters panties and pantyhose and wearing them to bed

Flip Wilson, Milton Berle, 3 stooges, ..

Quote:

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Originally Posted by Robbiegirl

In both real life and in Media ?

For those of us who are older, and before the internet there were few and far oppurtunties to see guys dressed as women so at least for me everyone of them sticks in my mind. I will only mention a few and hope you will share yours . Do others have strong memories like mine.

The one thing that never changed was that all the situations were comical and the women I was with found it way more amusing than the men.

The First was going to see the Vienna Boys choir with my family. After several fun skits almost half the boys came out in pretty peasent dresses, petticoats and wigs and proceeeded to sing and dance around like silly girls ! the audience loved it and it was my sisters favorite part of the show. I was jealous of how cute the boys were in their dresses.


The second was attending a popular TV game show in LA called " Truth or Consequences " in person with my family and crazy Aunt Ann.

When the curtins opened two men from the studio audience were on the stage in robes accompanied by the pretty display models (picture Vanna White), with suitcases in front of them. The audience was told that the fastest one to get dressed would get $100 and the other $50 When the horn was blown the men took off their robes to reveal they were in white briefs that looked more feminine than masculine. When the suitcases were oped by the models it became clear to everyone that they were filled with beautiful Feminine clothing. Starting from the top with the minimal help and guidence from the models the men raced to put on Lacy Stuffed Bras, squeezed into Panty Girdles ( my mom's girlfriend Ann's favorite part) put on stockings and attached them to the garters, stepped into a beautiful silky & lacy Full Slip, put on heels, stepped into and were zipped into a feminine dress, put on a Jackie O type hat and had to grab a purse and walk to the other end of the stage. Ann said it took all of about 4 minutes but was the funniest thing her and her girlfriend had ever seen, she said it was so fun to see men have to put on and wear women's things! My sisters and mom thought it was terribly funny and loved the story, my dad and I were not as convinced. Our reaction was noted by mom and for several minutes the ladies attempted to get us to try the "The Suitcase Race" But my dad would not go for it. So everytime I watched the show I wondered if they used that skit ever again ?

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Holy Moly, I remember seeing that episode on broadcast TV!! My grandmother was over and she was howling with laughter.

When I was a teenager my friends and I were out way too late in a part of town we weren't really supposed to be in and while we were being teenagers on the sidewalk a man walked by and went into a local bar a little ways down. She was very tall and wearing a floral dress with low heeled pumps. I remember at the time I thought she looked intimidating but now I know she was probably more scared of us.

Probably Springer or Maury Povich. The episodes that stuck with me the most were those "this was me in high school, look at me now episodes" where they would show a picture of skinny guy and then they'd come out looking gorgeous dressed like a woman, I was fascinated by that as a kid

Milton Berle would have to be the first one I remember seeing but it made no impact on me because I was a kid.

Maybe impact was the wrong word ! My point being just the idea of guys being able to dress as women.

Who can forget Ricky Schroder in Silver spoonsAttachment 271237

Milton Berle would probably be first. Many came after, Klinger, Flip Wilson, Bennie Hill, Tootsie, Mrs. Doubtfire, a cartoon in Playboy magazine of a guy in stockings and a slip singing "Don we now our gay apparel." (very inappropriate!) and probably hundreds more! They were not however an influence in me being a CD! Respectfully Hugs Lana Mae

I can't remember a time when I didn't enjoy crossdressing, however I was always taught that it was a shameful thing for a boy to do. Then when I was six years old my family traveled across several states to visit an uncle. He was happy to see us and showed us around. At one point my uncle pulled out a bunch of pictures. He instructed us about each picture and then we came to a set of photos of a woman in a formal gown with petticoats and wearing a mask. "That was Halloween", my uncle excitedly proclaimed. "I came as a princess and everyone thought I was woman." He was so proud of how he looked as a woman. He told us about how he got the wig and dress. I stared at those pictures a long time. He did make a good looking woman. My mom and several other women complimented my uncle. I was dumbstruck. Here was a case where a man could dress as a woman and nobody told him he should be ashamed of himself. I so wished I could do something like that. That was over 50 years ago and I can still see that picture in my mind.

One not mentioned yet that I remember was a short lived 60s TV show called "The Ugliest Girl in Town." (Yes the title was politically incorrect, but it was the 60s after all.) It starred Peter Kastner doing drag a la the much later Tootsie. I remember as an early teen, and early CD, sneaking off to our second TV (in the kitchen no less) and being memorized by this guy openly wearing women's clothes. I wanted to be him. Peter's star was on the rise when he accepted the role of Tim/Timmie. When the show quickly closed Peter never again saw a starring role. Sad really. You can find a few early episodes on YouTube, if you are so inclined.

Lana Mae, I so remember that cartoon in Playboy and think about it everytime that song is sang around Christmas Time

For me it was probably Milton Berle and Flip Wilson. I remember mostly Flip Wilson as he went all the way with the dressing up including panties.

I guess that Flip Wilson was the first that got my attention due to the fact that he went all the way besides just being so entertaining. As for seeing a real CD I go back to the 70s when my wife and I went to Finocchios in San Fran while exploring the west coast. I was mesmerized by that show for days.

For a local memory, I remember seeing a pretty well dolled up CD shopping in Frugal Fannies in MA while shopping for some cloths in the 80s. I don't remember the details but she really got my attention and I did my discreet best to follow her without drawing attention.

Like many have said, my first exposure must have been Milton Berle, then Flip Wilson and of course Benny Hill. Other vivid memory are Jack Lemon and Tony Curtis in Some Like it Hot.

Definitely Monty Python for me. Where I grew up PBS was a VHF channel (13), so I was raised by British television.