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:<3:

[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.

[noeleena]

Hi,

Some time in the 50's to 60's or a bit later there was something about a group doing this , though i dont belive our trades school did it we were both young men & women, though i have done a stint for a church group in the 50's .

...noeleena...

[linda allen]

The problem with these events, plays, etc. (and Halloween dressing also) is that if you do too good a job, you give people reason to believe this isn't your first time and that you might be a secret crossdresser. A high school student, or even a typical male dressed as a female for Halloween wouldn't likely have a pair of $400 breast forms, a $200 wig, padded panties, complete makeup (and know how to apply it), womwn's shoes, etc.

[Jessica Keys]

Our school did the freshmen initiation each year when you moved into the ninth grade.
About the third week of the new school year on a Friday the freshmen would find written on the blackboard what was required to be worn the following Monday.
The girls always got to wear overalls over a farm type shirt. Of course they wore their girl shorts under this for wear after school.

The boys were the feature attraction you might say as we had to fully dress the part. No boy underthings were allowed.
My year the boys were required to wear a sun dress at least two inches above the knee. Two inch or higher heels. A bra and garter belt hooked to nylons and of course panties. I was already dressing on the secret from my mom. But this would be the first time I was actually out in public. Little did I know then.
My mom was larger then me so that Saturday morning she asked a younger neighbor lady if she had a spare garter belt and panties for me. I wasn't too happy to hear my mom asked her for those items and we had a small argument to which my mom opened the bathroom door where the paddle always hung. I shut up.
Later that afternoon the door bell rang and my mom called me into the front room and the neighbor lady handed me a sack with the items smiling fully.
Years later I would see her and she always asked if I needed to borrow anything. Did she know I??? A missed opportunity I believe.
I rode my boys bicycle to school that morning as my mom worked. I found out why girls don't have a cross bar.
Of course upon arriving at school that morning I was met by seniors with lip stick and such.
More to the story...... but the same school now bans such things.
I use to have some pictures of me dressed in a photo album but years ago I took them out and burned them. One of my purge's I did then.

[Cheryl Ann Owens]

The problem with these events, plays, etc. (and Halloween dressing also) is that if you do too good a job, you give people reason to believe this isn't your first time and that you might be a secret crossdresser. A high school student, or even a typical male dressed as a female for Halloween wouldn't likely have a pair of $400 breast forms, a $200 wig, padded panties, complete makeup (and know how to apply it), womwn's shoes, etc.

Linda, You're absolutely right. When I was 29 my wife and another couple went to a Haloween party at a classy country club among many other friends. I'm sure I did it too well and people treated me in a way I could just "tell" that I was almost outing myself. I wore a bridesmaid gown that looked like an evening gown, perfect makeup and all. I also think many of my subtle mannerisms such as seating myself as a woman would, the way I walked, etc. were other visual cues. So much for flying under the radar......

Cheryl Ann

[NV Susan]

I never had the chance to CD at high school.....sure would have made going to school a LOT more fun!!

[Aly Cat]

I wore underthings all through high school. Though for me it was a bit different. I was home schooled from second grade through twelfth so when I would get up in the morning, I would sneak into my sisters room (she was already at work by then) swipe a cute pair of satin thong panties and would head to the bathroom to brush my teeth and get ready for the day. When I would get into the bathroom, Id put them on with the satin nightie she would leave hanging on hook in the bathroom and I would wear them while brushing my teeth and getting ready pretending I was a girl. When I was done, I would change back into my boy clothes and put everything back exactly how I found it and then go about my day. On rare occasions, Id keep the thong on under my boys underwear for the day but I was afraid of getting them dirty so I didnt do that often...I was paranoid about being found out and was afraid my sister would recognize a pair in the hamper that was dirty that she didnt wear.

Of course now I totally kick myself for being so stupid! My sister pried my secret out of me about 3 months ago by sharing a secret of her own that I figured was worthy material. When I told her, she was like...OMG! Why didnt you tell me?!? We were best friends! I could have been buying panties and clothes and stuff for you all this time and covering for you from Mom and Dad. Then you wouldnt have had to go through that alone! My breath was literally taken away by how accepting she was and it was literally one of the happiest days I have felt in years. Of course, after that, I literally facepalmed myself thinking I wasted all that time being paranoid and afraid when I could have had GG ally!

[Krista1985]

There was a powder-puff football event at my HS where the cheerleaders played (flag) football while members of the football team dressed as cheerleaders. The gals would play on the field in full pads with helmets, and the guys would be in skirts and jumpers off to the side doing some cheers they rehearsed earlier in the week. I think 10 or so of the 50+ varsity players volunteered to be cheerleaders. Did I participate? No I wasn't on the football team (soccer rules) and at that point a very masculine dude. CDing had not yet occurred to me back then, in fact I went out of the way to avoid doing feminine things. Maybe it was some sort of denial enforced, over-compensating coping mechanism, who knows?

College on the other hand... lets just say that more than one fraternity on every college campus in the USA makes their pledges CD for one reason or another. I can remember borrowing a dress from a female friend for a mixer where my pledge brothers and I were made up by sorority pledges to serve drinks. We were beer wenches, and ugly ones at that. Our old albums had pictures of every class going back for decades doing the same thing. Ahh hazing. To think I didn't have anything of my own back then, or for a few years after. I guess that was my first time cding, even though I was only going along with the program and doing it as a means to an end. I didn't repeat the behavior for a few years after, and then for entirely personal reasons.

[joanna4]

Yes this was common. There were guys dressed in the girls cheerleading uniforms and with no wig or makeup, just the skirt and shell. I wished I could have participated. We did not have a crossdressing day or an opposite day but there's always halloween.

[joanne_mi]

The problem with these events, plays, etc. (and Halloween dressing also) is that if you do too good a job, you give people reason to believe this isn't your first time and that you might be a secret crossdresser. A high school student, or even a typical male dressed as a female for Halloween wouldn't likely have a pair of $400 breast forms, a $200 wig, padded panties, complete makeup (and know how to apply it), womwn's shoes, etc.

Bingo. Of course I grew up in Redneckistan where this sort of thing wouldn't have been taken lightly.