Top Ten Childhood Mindblowing Moments

[michelleddg]

I'm sure you've had these too, especially if you grew up pre-internet. Moments of men wearing women's clothing that just left me gasping for air in my formulative years and are still as vivid as ever in my memory. Hugs, Michelle

1) Jim Bailey appearing on Ed Sullivan. Ed introduced him in boy mode, then half an hour later he performed as Judy Garland or Peggy Lee.
2) A Dear Abby column in which a young lady visits a couple. The first night they went to the ballpark. The second night a stunning, statuesque blond came down the stairs...it was him! "I just do this for kicks", he advised. The three girls went out on the town.
3) A friend in the 5th grade fully dolled up for Halloween. I remember especially the wig, lipstick, nylons and high heels. Don't think he had a garter belt, just kept on rolling his nylons up, and he kept matter-of-factly complaining about the high heels.
4) Christopher Morley in Freebie and the Bean.
5) Christopher Morley in a Playboy photo spread in which he and a girl exchange clothes.
6) Jeff Bridges in Thunderbolt and Lightfoot.
7) A comic strip with a police theme. The perp says "I've fooled policemen in five states dressed like this, how did you read me?" "No real woman would miss the run in her nylons."
8) An Archie comic in which he's frustrated about how long Betty and Veronica take to get ready, so gets totally dolled up in record time to show it can be done.
9) A shaving cream commercial in which an undercover agent needs a really close shave to pose as a female. He's gorgeous...the voiceover says "great face...but that body!".
10) Ted Bessell, Marlo Thomas's boyfriend on That Girl, crossdressing.

[Angela Campbell]

Joe Namath wearing pantyhose!
The Beatles wearing long hair (The hair was so long it actually touched the ears! at the time it was a big deal)
David Bowie wearing a mini skirt

[Kate Simmons]

I think they need to put out a DVD about this to entice CDers to subscribe to Time magazine.

[Taylor186]

Watching the short lived (1968-69) TV series "The Ugliest Girl in Town."

" ... It ran from September 26, 1968 to January 30, 1969. Timothy Blair is a Hollywood talent agent. He falls in love with Julie Renfield, a British actress who is visiting the United States to do a movie. After that movie is finished, she returns to England. To assist his brother Gene complete a photography assignment, Timothy dresses as a hippie and poses for a photo shoot. The photos are sent to a modeling agent in England who assumes that they are of a woman. He offers "her" a job.

Knowing that this would be the only chance to go to Great Britain and be with Julie, Tim accepts and dubs himself "Timmie." Tim has two weeks of vacation to spend as much time with Julie as he can, but when as he is about to leave with his brother, Gene loses £11,000 gambling. Unless he pays him back, Tim has to continue being Timmie for a while longer." (from Wiki)

Yeah, sounds like a fictionmania story. My parents thought I was crazy. Little did they know. You can find the premier episode in youtube.

[Jodie_Lynn]

Bugs Bunny and Daffy Duck crossdressing in order to fool Elmer Fudd. I always wondered how Bugs could apply his lipstick so quickly........

[rocketscientist]

Some of my earliest memories of crossdressing in media include the tv show "Bosom Buddies" that starred Tom Hanks and Peter Scolari as roommates that dressed to fool the landlord so they could stay for cheap in an all girl apartment house. Another movie I remember very well (probably because I have it on video!) is "Private School" that starred many big names at the time, including Phoebe Cates, Betsy(OMG) Russell, Matthew Modine, and a sidesplitting turn by the late, great Ray Walston. In it there is a great scene where 3 of the guys crossdress in order to infiltrate the neighboring all girl "Cherryvale Academy". Priceless!

[Julie Bender]

Gillagan's island!lots of cd episodes lol
Gillagan dressed as a woman to fool cannibables!
The skipper dressed once and the professor also dressed l watched that show daily multiple times a day at times!

[marlenesexton]

Bosom Buddies has to be one of mine. Bug Bunny too. The various Jerry Springer-esque day time shows. When I discovered the women with penises I fantasized about actually existed in the form of transsexuals. The entire pantyhose culture of the 80s.

I had to amend mine after reading Lisagurl's reply. One Halloween my mom dressed me up in her clothes, pantyhose, heels, dress, even an old wig and makeup. I was getting "too old," ten or twelve maybe, but decided to go last minute with some friends. Nothing weird, just desperation. I'm not sure if she knew I was already dressing up in her things (she probably did) but going out and visiting all the neighbors dressed was heavenly.

[NathalieX66]

Seeing KISS perform on tv in 1976, hosted by Paul Lynde. I was aged 10, and forever ruined.

[daviolin]

Some like it Hot. I saw this movie in the theater back in 1957. I was nine years old. Oh yea! I was in awh. Daviolin

[il.dso]

Interesting topic.
i remember a James Bond movie where one of the villains was beautifully dressed as a woman.
Not sure which movie it was...

[lisagurl]

when my aunt dressed me up as a girl at age 10 just being silly and goofy............then when i went home i began off and on dressing as a girl, started with my moms panties.....

[MsJordan]

Dr. Jekyll & Mrs. Hyde, Switch, He's A Lady (The reality show that really prompted me to give cd-ing a try), the talk shows of the 90s & early 00's where the audience had to guess if it was a man or a woman fascinated me, pantyhose commercials/ads, and when RuPaul first came on the scene!

[Tina B.]

You people make me feel old, first childhood memories of a man in a dress getting my attention would be, either Red Skelton, or Milton Berle. Neither was very good looking, trying for the big laugh, old grandma dresses, bad wigs, and to much makeup, but to me it was something I waited all week in hopes that either of them would wear it again, them and the Sear and Roebuck caralog got me through my childhood during the dark ages of the 50's.

[Cheryl Ann Owens]

For me it was watching Christine Jorgensen in her first appearance on the Mike Douglas Show. I was glued to the set! Then when her movie came out Mom insisted we go to the drive-in to see it. I wonder if she knew??????

Then when I was around 15 and walking around one Haloween night with a friend. (Not costumed) We met up with a 12 yr old whose mother went all out to dress him with pantyhose, dark wig, and full makeup, and heels. He could easily pass and I was SOOOOO jealous!

Then my junior year in high school dating a gal who really wanted to do full makeup on me because of my "pretty blue eyes" and I declined!

Cheryl Ann

[Beverley Sims]

Ajax lipstick is not sold in stores.
Try buying it on line from Bugs Bunny enterprises.

[Taylor186]

Forgot to mention The Flip Wilson Show.

[michelleddg]

Taylor, The Ugliest Girl In Town, and Flip Wilson - those are good ones! Reminded me of the annual appearance of the drag queen Beverly Lasalle on All In The Family. Hugs, Michelle

[LilSissyStevie]

Little Lord Fauntleroy - A sissy that whipped the bad guys. My hero!

The cover of We're Only In It For The Money - The Mothers Of Invention. Frank Zappa in a dress was totally cool.

Tiny Tim, Truman Capote, Liberace. They were GQ (the other kind, not the magazine) before it was a college course.

[Farrah]

When Rick Schroeder dressed as a girl/his date on Silver Spoons, Dr. Jekyll and Ms. Hyde, Too Wong Foo, The talk shows during the 90's (I saw my first TS on Oprah) I had heard of sex changes, but I didn't think it could be done.

[flatlander_48]

Some like it Hot. I saw this movie in the theater back in 1957. I was nine years old. Oh yea! I was in awh. Daviolin

YES!! My mother and aunt were big movie fans and they often took me with them. Actually it was 1959 and I was 11...

You people make me feel old, first childhood memories of a man in a dress getting my attention would be, either Red Skelton, or Milton Berle. Neither was very good looking, trying for the big laugh, old grandma dresses, bad wigs, and to much makeup, but to me it was something I waited all week in hopes that either of them would wear it again, them and the Sear and Roebuck caralog got me through my childhood during the dark ages of the 50's.

Also Jonathan Winters as Maudie Frickert. Wacked, just totally wacked...

[RADER]

I remember all the news stories about Christine Jorgensen.
That was an earth moving event at the time. Just Imagen,
A boy changing into a girl. I must have read everything 3 times.
Rader

[Jodie_Lynn]

Oh, I almost forgot my favorite Star Trek episode, when one of Kirk's old GF's transfers her mind into his body, and his into hers. Shatner's performance was great, and really spurred my desire to explore space......

[Alison Lewis]

When Rick Schroeder dressed as a girl/his date on Silver Spoons, Dr. Jekyll and Ms. Hyde, Too Wong Foo, The talk shows during the 90's (I saw my first TS on Oprah) I had heard of sex changes, but I didn't think it could be done.

Ricky Schroeder was a major one for me. At the time, I remember feeling bad for his character. Some time later, after my CD was sparked, I later became jealous of his predicament.

[BillieJoEllen]

Interesting topic.
i remember a James Bond movie where one of the villains was beautifully dressed as a woman.
Not sure which movie it was...

I too remember a James Bond movie that had a man dressed as a woman but it wasn't revealed until the end of the movie. Any body else remember?