Crossdressing in high school

[shayleetv]

I was surfing the net the other day and came a crossed a site that I found quite interesting. I've seen it mentioned hear before, it's femulate.org. on this site she has a link to a flicker page called "Stana Stana" on this site she has a friend that finds pictures of boys in yearbooks that are dressed as girls for activities for school. Some are womanless pageants, some are plays where there* are all boy performance, some are mock beauty pageants and some are for cross dressing day during spirit week. After looking at some of these pictures I got a twinge of jealousy. We never had anything like this when I was in school.

MY BIG QUESTION IS DID ANY OF YOU HAVE THESE ACTIVITIES AND IF YOU DID, DID YOU PARTICIPATE. I know I would have. Some of those boys are quite comely if not downright gorgeous.

[Beverley Sims]

Yes I was lucky, I was a boy soprano and sang a song in a concert dressed as a girl.
My parents were not impressed but everyone else was.
Me I just had to enjoy the moment.

[Karren H]

We had a couple crossdressing events in High School... one being the Varsity club initiation where you had to dress as a girl all school day.... The year before I was eligible there was this on small guy who made an amazing girl.... fishnets and short skirt and perfect makeup... you could tell by the way he walked he had done that before.... my luck was the year I was eligible they abolished the initiation! sigh.... I was all ready too!

At our kids High School a few years ago.... it was nothing to see 3 or 4 boys crossdressed at every event.... they looked really convincing....

[DonnaT]

Back in the 70's, when I went to high school, there was one event, a pep rally, where some of the football players dressed as cheerleaders and some of the cheerleaders dressed as football players.

I wasn't asked to participate, and as shy as I was, no matter how much I would have wanted to, I wouldn't have been able to get past the shyness.

The closest I got was during my senior year, the seniors put on a play, and I got to have one of the girls put makeup on me.

When my daughter was in high school, they had a senior day/night, where the seniors spent the day and night at the local gym/pool partying. There was a womanless beauty pageant that night.

[Kate Simmons]

Little did they know in HS that I did my own initiation at home every Friday afternoon when my Mom took my Grandma to the store.

[Tracii G]

We never had events like that when I was in HS.
I did go to the prom as a girl one time which was fun.

[stepanie]

I never had a crossdresssing event in school but I was in several plays. During a dress rehearsal for one play the girl that was doing my make-up got finished stepped back to check her work, calls a friend over to inspect her work as well, they both whisper something to each other and thenone that put the make-up on me leans in and apolligeticaly tells me I look like a girl with this make-up on. I didn't think much of it then, although, at 15 with hormones raging and this 17 year old hottie telling me I looked like a girl I wasn't all that happy about it but I wasn't all that worried about it either. Maybe this is why I like to try on make-up now...Hmmm.

[giuseppina]

There wasn't anything like this at my HS, and even if there was, I wouldn't participate for personal safety reasons. I had a lot of problems with bullying.

[sometimes_miss]

Of course even back in the sixties, you could on halloween find a few boys dressed up as girls, some who were so perfect for it body and face wise that it amazed everyone. I already was being made fun of for different reasons, so I never had the courage to dress up as a girl for halloween when I was a kid.

[~Joanne~]

When i went to school, we had the cross gender day during spirit week. The girls all did it, a few guys did it but didn't do it all together if you know what I mean. they looked horrible. I never did it myself but I should have but back then all I wore is hose so I didn't.

[stacy-marie hanna]

at the end of year 9 at my school,as part of our drama lesson we had to put on a 20 minute play.the group i was in consisted of 5 guys and we did a jerry springer style tv show.
the plot was the guy had multiple wives he'd kept secret from each other,his 3 wives were me and 2 of the lads dressed enfemme.
stacy-marie

[Cheryl Ann Owens]

My sister wanted to dress me up as a girl for Haloween and I refused! What was I thinking???!!! Kick me!

Cheryl Ann

[Sometimes Steffi]

Yeah, right.

The main crossgressing thing I remember in high school was this.

Someone came up with this gender test.

Look at your finger nails. If you hold your hand out flat with the back facing you you're a girl. If you ball your hand into a fist and turn the palms toward you, you are a boy. One of the prettiest girls turned out to be a girl. One of the girls with "a good personality" turned out to be a boy.

As for me, when I was asked, my hands were flat on the desk in front of me palms to the desk and back facing me. Without moving my hands, I just tilted my head down and looked at my hands. The conclusion of the "experts" was that the results were inconclusive.

Even though the "test" was meaningless, I don't think I could have lived down showing up as a girl in the gender test.

But, maybe if the experts thought out of the box, the answer would have been both, or some from column B and some from column G.

The test was

[Ciara Brianne]

I did a Monty python skit with some friends for a high school talent show. Now that I think about it, that was the first time I dressed in public. It was a riot. We knew that dressing up was going to get us teased, so we practiced a lot on the skit. We were booed and taunted when we first came on stage, but within a minute of starting the skit the audience was in laughter. We got second place. The first place winner was my friends band, with their big hair and spandex. lol They had on more makeup than we did.

I had a girlfriend who wanted to dress me up for Halloween. When she mentioned it, I played like I didn't want to, hoping she would press the issue. She didn't. I was kinda bummed.


Ciara

[Monique53]

When I was in high school(late 60's--early 70's), there were no events like that. Of course, I live in the Deep South and so it was a very conservative time and place( Bubba in the pickup trucks with rifle racks in style at the time). I did,however, have the opportunity, with a couple of my wild friends to dress up as a nun, at Halloween( some may remember the three singing nuns from that era) and had a great time with my black pantyhose and lace up women's heels. I got told that I looked like a Catholic school principal, Haha!!!

Monique

[MisterEgurl]

Oh, I wish, I wish, I WISH!!! 12 years of catholic schools here. The big letting down of the dress code during Homecoming week was "funky tie day" or Casual Day where us guys could wear any pair of non-denim slacks, non-sneakers and the non-school polo shirt of our choice.

Having hair that hung over your collar was a detention. Gender inappropriate attire would have gotten an expulsion.

Oh, if we had a cross-dressing day... I would have LOVED to wear the girls uniform. I knew EXACTLY what combination of skirt, blouse, tights, and shoes I would have worn.

[Sheila11]

Did a cheerleader skit at a no talent night in college and was part of a cheerleader squad during a powder puff football game.

[Julogden]

When I was in high school, the only event along those lines was when the football team dressed as cheerleaders and the cheerleaders played a game of football. I wasn't on the football team, and somehow didn't see this event in person.

I've seen Stana Stana's photos on the page you mentioned, also on her Flickr page and it is indeed amazing to see. I also noticed that the schools having crossdressing days and womanless pageants seem to be more in southern states than up north. I wonder why that's more common down south?

Carol

[linda allen]

I worked in a public high school (this was about ten years ago) and there was a boy student who was apparently transgender and dressed and acted as a female every day, all day. He (she) even used the girls rest room. The other girls looked out for him (her).

Remember of course, most high school girls don't wear dresses, skirts, etc., to school anymore so his (her) outfit was usually feminine jeans and casual blouses. No boobs.

[MarcyRex]

Back in my Junior High/Middle school, there was a annual fundraising event called Slave Day or Maid and Butler day. Kids (10 male/10 female selected) signed up to auction the use of their services during the school day. The bidding was always a fun filled event. Much anticipation for the following day. Carrying the books around and offacious announcements upon classroom entry all in good fun. The costumes ranged from simple crazy hats to french maids/ballerinas. Naturally much giggling and embarrasment was done. This ended after some complaints and became much more tame.

[Cathy Jooste]

I played a lead part in our school musical and had to wear a girls leotard and tights. The girls had fun teasing me and told me I had sexy legs. It was such fun!!!!

[Geena75]

I had a friend who was singing "Sweet Gypsy Rose" in a talent show, and wanted me to dress as "Rose" and come on stage at the end of the song. I declined, and he got someone else. I think I didn't want to open that door at that point in life. Often wondered what would have happened if I had.

[ept_guy]

that would of been so hot!!!!

[chris80]

In the early 60's at my all boys school we did a play in modern dress. The lucky 'female' lead wore two very full skirted dresses. I cannot remember the play but still have that vision in my mind's eye. Jealous,moi? unfortunately there were never any photos in the school magazine

[Terraforming]

We had a day during spirit week where the seniors would gender swap for a rally. I tend to look back on it with embarrassment though, since I didn't have a clue what I was doing back then.